Novel heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides

ABSTRACT

The present invention relates to novel heteroaryl-triazole and heteroaryl-tetrazole compounds of the general formula (I), in which the structural elements Y, Q 1 , Q 2 , R 1 , R 2 , R 3a , R 3b , R 4  and R 5  have the meaning given in the description, to formulations and compositions comprising such compounds and for their use in the control of animal pests including arthropods and insects in plant protection and to their use for control of ectoparasites on animals.

The present invention relates to novel heteroaryl-triazole andheteroaryl-tetrazole compounds, to formulations and compositionscomprising such compounds and to their use in the control of animalpests including arthropods and insects in plant protection and to theiruse for the control of ectoparasites on animals.

Certain heteroaryl-triazole and heteroaryl-tetrazole compounds offormula I (R^(3b)=hydrogen) are disclosed for the use in controllingectoparasites on animals in WO 2017/192385.

Modern plant protection products and veterinary ectoparasiticides haveto meet many demands, for example in relation to efficacy, persistence,spectrum and resistance breaking properties. Questions of toxicity, thecombinability with other active compounds or formulation auxiliariesplay a role, as well as the question of the expense that the synthesisof an active compound requires. Furthermore, resistances may occur. Forall these reasons, the search for novel crop protection compositions orveterinary ectoparasiticides cannot be considered to be complete, andthere is a constant need for novel compounds having properties which,compared to the known compounds, are improved at least in respect ofindividual aspects.

It was an object of the present invention to provide compounds whichwiden the spectrum of the pesticides in various aspects.

The present invention therefore provides compounds of the generalformula (I)

in which (Configuration 1-1):

-   X is O or S;-   Q¹ and Q² are independently CR⁵ or N, provided at least one of Q¹    and Q² is N;-   Y is a direct bond or CH₂;-   R¹ is hydrogen; C₁-C₆alkyl optionally substituted with one    substituent selected from —CN, —CONH₂, —COOH, —NO₂ and —Si(CH₃)₃;    C₁-C₆haloalkyl; C₂-C₆alkenyl; C₂-C₆haloalkenyl; C₂-C₆alkynyl;    C₂-C₆haloalkynyl; C₃-C₄cycloalkyl-C₁-C₂alkyl- wherein the    C₃-C₄cycloalkyl is optionally substituted with one or two halogen    atoms; oxetan-3-yl-CH₂— or benzyl optionally substituted with    halogen or C₁-C₃haloalkyl;-   R² is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein    the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is    substituted with one to five substituents, provided at least one    substituent is on either carbon adjacent to the carbon bonded to the    C═X group, each independently selected from the group consisting of    halogen, hydroxy, —NH₂, —CN, —SF₅, —COOH, —CONH₂, —NO₂, or in each    case optionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl,    C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy,    C₁-C₃haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,    C₁-C₆alkylsulfonyl, C₁-C₃haloalkylthio, C₃-C₆cycloalkylsulfanyl,    C₃-C₆cycloalkylsulfinyl, C₃-C₆cycloalkylsulfonyl,    C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl, phenylsulfanyl,    phenylsulfinyl, phenylsulfonyl, —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂,    —NHCO—C₁-C₄alkyl, —N(C₁-C₄alkyl)CO—C₁-C₄alkyl, —NHCO-phenyl,    —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂,    —CONH(C₃-C₆cycloalkyl), —CON(C₁-C₄alkyl)(C₃-C₆cycloalkyl),    —C(═NOC₁-C₄alkyl)H, —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl; phenyl and 5- to    6-membered heteroaryl, wherein the phenyl or 5- to 6-membered    heteroaryl is optionally substituted with one to two substituents,    each independently selected from the group consisting of halogen,    —CN, in each case optionally substituted C₁-C₆alkyl, C₁-C₃haloalkyl    and C₁-C₄alkoxy; or-   R² is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein    the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is    substituted with a total of one to three substituents, provided the    substituent(s) are not on either carbon adjacent to the carbon    bonded to the C═X group and at least one and up to three    substituent(s) are independently selected from group A consisting of    C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,    C₃-C₆cycloalkylsulfanyl, C₃-C₆cycloalkylsulfinyl,    C₃-C₆cycloalkylsulfonyl, C₁-C₃haloalkylsulfinyl,    C₁-C₃haloalkylsulfonyl, in each case optionally substituted    C₃-C₆cycloalkyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl,    —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl,    —N(C₁-C₄alkyl)CO—C₁-C₄alkyl —NHCO-phenyl, —CO₂C₁-C₄alkyl,    —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂, —CONH(C₃-C₆cycloalkyl),    —CON(C₁-C₄alkyl)(C₃-C₆cycloalkyl), —C(═NOC₁-C₄alkyl)H,    —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl; phenyl and 5- to 6-membered    heteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl is    optionally substituted with one to two substituents, each    independently selected from the group consisting of halogen, —CN, in    each case optionally substituted C₁-C₆alkyl, C₁-C₃haloalkyl,    C₁-C₄alkoxy and C₁-C₄haloalkoxy;    -   the other one to two optional substituent(s) are each        independently selected from group B consisting of halogen,        hydroxy, —NH₂, —CN, —SF₅, —COOH, —CONH₂, —NO₂, in each case        optionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl,        C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy,        C₁-C₃haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,        C₁-C₆alkylsulfonyl, C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl,        C₁-C₃haloalkylsulfonyl, phenylsulfanyl, phenylsulfinyl,        phenylsulfonyl, —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂,        —NHCO—C₁-C₄alkyl, —N(C₁-C₄alkyl)CO—C₁-C₄alkyl, —NHCO-phenyl,        —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂,        —CONH(C₃-C₆cycloalkyl), —CON(C₁-C₄alkyl)(C₃-C₆cycloalkyl),        —C(═NOC₁-C₄alkyl)H, —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl; phenyl and 5-        to 6-membered heteroaryl, wherein the phenyl or 5- to 6-membered        heteroaryl is optionally substituted with one to two        substituents, each independently selected from the group        consisting of halogen, —CN, in each case optionally substituted        C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy;    -   or-   R² is naphthyl optionally substituted by one to three substituents    independently selected from the group consisting of halogen,    hydroxy, —CN, —COOH, —CONH₂, —NO₂, —SF₅, —NH₂, in each case    optionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl,    C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy,    C₁-C₃haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,    C₁-C₆alkylsulfonyl, C₃-C₆cycloalkylsulfanyl,    C₃-C₆cycloalkylsulfinyl, C₃-C₆cycloalkylsulfonyl,    C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl,    phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, —NH(C₁-C₄alkyl),    —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl, —N(C₁-C₄alkyl)CO—C₁-C₄alkyl,    —NHCO-phenyl, —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂,    —C(═NOC₁-C₄alkyl)H, —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl; phenyl and 5- to    6-membered heteroaryl, wherein the phenyl or 5- to 6-membered    heteroaryl is optionally substituted with one to two substituents,    each independently selected from the group consisting of halogen,    —CN, in each case optionally substituted C₁-C₆alkyl, C₁-C₃haloalkyl    and C₁-C₄alkoxy;    -   or-   R² is a heterocyclic ring which is selected from the group    consisting of 4- to 10-membered saturated and partially unsaturated    heterocyclyl, 5-membered heteroaryl, 9-membered heteroaryl and    10-membered heteroaryl, each of which is optionally substituted by    one to three substituents independently selected from the group    consisting of halogen, ═O (oxo), hydroxy, —CN, —COOH, —CONH₂, —NO₂,    —SF₅, —NH₂, in each case optionally substituted C₁-C₆alkyl,    C₃-C₆cycloalkyl, C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₃haloalkyl,    C₁-C₄alkoxy, C₁-C₃haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,    C₁-C₆alkylsulfonyl, C₃-C₆cycloalkylsulfanyl,    C₃-C₆cycloalkylsulfinyl, C₃-C₆cycloalkylsulfonyl,    C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl,    phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, —NH(C₁-C₄alkyl),    —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl, —N(C₁-C₄alkyl)CO—C₁-C₄alkyl,    —NHCO-phenyl, —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂,    —C(═NOC₁-C₄alkyl)H, —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl; phenyl and 5- to    6-membered heteroaryl, wherein the phenyl or 5- to 6-membered    heteroaryl is optionally substituted with one to two substituents,    each independently selected from the group consisting of halogen,    —CN, in each case optionally substituted C₁-C₆alkyl, C₁-C₃haloalkyl    and C₁-C₄alkoxy;    -   or-   R² is in each case optionally substituted C₁-C₆alkyl,    C₃-C₆cycloalkyl or C₁-C₆haloalkyl;-   R^(3a), R^(3b) are independently selected from the group consisting    of hydrogen; halogen; —CN; C₁-C₆alkyl optionally substituted by one    to three substituents independently selected from the group    consisting of halogen, hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, in    each case optionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl,    C₁-C₄alkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,    —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl,    —N(C₁-C₄alkyl)CO—C₁-C₄alkyl, —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), and    —CON(C₁-C₄alkyl)₂; optionally substituted C₃-C₆cycloalkyl;    optionally substituted C₁-C₆haloalkyl; optionally substituted    C₂-C₆alkenyl; optionally substituted C₂-C₆haloalkenyl; optionally    substituted C₂-C₆alkynyl; benzyl wherein the phenyl substituent is    optionally substituted with one to five substituents, each    independently selected from the group consisting of halogen,    hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, —SF₅, in each case    optionally substituted C₁-C₆alkyl, C₁-C₄alkoxy, C₁-C₃alkylthio,    C₁-C₃alkylsulfinyl, and C₁-C₃alkylsulfonyl; heterocyclyl-C₁-C₆alkyl    wherein the heterocyclyl substituent is selected from the group    consisting of 4- to 10-membered saturated and partially unsaturated    heterocyclyl, 5-membered heteroaryl and 6-membered heteroaryl, each    of which is optionally substituted by one to three substituents    independently selected from the group consisting of halogen, ═O    (oxo), hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, in each case    optionally substituted C₁-C₆alkyl, and C₁-C₄alkoxy; phenyl    optionally substituted with one to five substituents, each    independently selected from the group consisting of halogen,    hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH, —SF₅ in each case optionally    substituted C₁-C₆alkyl, C₁-C₄alkoxy, C₁-C₃alkylthio,    C₁-C₃alkylsulfinyl, and C₁-C₃alkylsulfonyl; or heterocyclyl wherein    the heterocyclyl substituent is selected from the group consisting    of 4- to 10-membered saturated and partially unsaturated    heterocyclyl, 5-membered heteroaryl and 6-membered heteroaryl, each    of which is optionally substituted by one to three substituents    independently selected from the group consisting of halogen, ═O    (oxo), hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, in each case    optionally substituted C₁-C₆alkyl, and C₁-C₄alkoxy;    -   or-   R^(3a), R^(3b) form together with the carbon to which they are    connected a C₃-C₆-carbocyclic or 3- to 6-membered heterocyclic ring    system, optionally substituted with one to two substituents, each    independently selected from the group consisting of halogen, —CN, in    each case optionally substituted C₁-C₆alkyl, C₁-C₄alkoxy and    C₁-C₃haloalkoxy;-   R⁴ is pyridine, pyrimidine, pyrazine, pyridazine or 5-membered    heteroaryl, wherein the pyridine, pyrimidine, pyrazine, pyridazine    or 5-membered heteroaryl is optionally substituted with one to three    substituents selected from the group consisting of halogen, hydroxy,    —CN, —COOH, —CONH₂, —CSNH₂, —NO₂, —NH₂, in each case optionally    substituted C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₃haloalkyl,    C₁-C₄alkoxy, C₁-C₃haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,    C₁-C₆alkylsulfonyl, C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl,    C₁-C₃haloalkylsulfonyl, —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂,    —NHCO—C₁-C₄alkyl, —NHCO—C₃-C₆cycloalkyl, —NHCO-phenyl,    —N(C₁-C₄alkyl)CO—C₁-C₄alkyl, —N(C₁-C₄alkyl)CO—C₃-C₆cycloalkyl,    —N(C₁-C₄alkyl)CO-phenyl, —N(SO₂C₁-C₃alkyl)₂, —NH(SO₂C₁-C₃alkyl),    —N(C₁-C₄alkyl)(SO₂C₁-C₃alkyl), —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl),    —CON(C₁-C₄alkyl)₂,    —C(═NOC₁-C₄alkyl)Hand-C(═NOC₁-C₄alkyl)-C₁-C₄alkyl;-   R⁵ is hydrogen, halogen, —CN, or in each case optionally substituted    C₁-C₃alkyl, C₃-C₄cycloalkyl, C₁-C₃alkoxy, C₁-C₃alkoxyC(O)—,    (C₁-C₃alkoxy)₂CH—, —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl),    —CON(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl, —N(C₁-C₄alkyl)CO—C₁-C₄alkyl,    —C(═NOC₁-C₄alkyl)H, or —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl.

The present invention furthermore provides compounds of the generalformula (I)

in which (Configuration 1-2)

-   X is O or S;-   Q¹ and Q² are independently CR⁵ or N, provided at least one of Q¹    and Q² is N;-   Y is a direct bond or optionally substituted CH₂;-   R¹ is hydrogen; C₁-C₆alkyl optionally substituted with one    substituent selected from —CN, —CONH₂, —COOH, —NO₂ and —Si(CH₃)₃;    C₁-C₆haloalkyl; C₂-C₆alkenyl; C₂-C₆haloalkenyl; C₂-C₆alkynyl;    C₂-C₆haloalkynyl; C₃-C₄cycloalkyl-C₁-C₂alkyl- wherein the    C₃-C₄cycloalkyl is optionally substituted with one or two halogen    atoms; oxetan-3-yl-CH₂— or benzyl optionally substituted with    halogen or C₁-C₃haloalkyl;-   R² is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein    the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is    substituted with one to five substituents, provided at least one    substituent is on either carbon adjacent to the carbon bonded to the    C═X group, each independently selected from the group consisting of    -   halogen, hydroxy, —NH₂, —CN, —SF₅, —COOH, —CONH₂, —NO₂,    -   and in each case optionally substituted C₁-C₆alkyl,        C₃-C₆cycloalkyl, C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₆haloalkyl,        C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio,        C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio,        C₃-C₆cycloalkylsulfanyl, C₃-C₆cycloalkylsulfinyl,        C₃-C₆cycloalkylsulfonyl, C₁-C₆haloalkylsulfinyl,        C₁-C₆haloalkylsulfonyl, phenylsulfanyl, phenylsulfinyl,        phenylsulfonyl, —NH(C₁-C₆alkyl), —N(C₁-C₆alkyl)₂,        —NHCO—C₁-C₆alkyl, —N(C₁-C₆alkyl)CO—C₁-C₆alkyl, —NHCO-phenyl,        —CO₂C₁-C₆alkyl, —CONH(C₁-C₆alkyl), —CON(C₁-C₆alkyl)₂,        —CONH(C₃-C₆cycloalkyl), —CON(C₁-C₆alkyl)(C₃-C₆cycloalkyl),        —C(═NOC₁-C₆alkyl)H, —C(═NOC₁-C₆alkyl)-C₁-C₆alkyl;    -   and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl        or 5- to 6-membered heteroaryl is optionally substituted with        one to two substituents, each independently selected from the        group consisting of halogen, —CN, in each case optionally        substituted C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy;    -   and an optionally substituted 4- to 6-membered saturated or        partially unsaturated heterocyclic ring;    -   or-   R² is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein    the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is    substituted with a total of one to three substituents, provided the    substituent(s) are not on either carbon adjacent to the carbon    bonded to the C═X group and at least one and up to three    substituent(s) are independently selected from group A consisting of    -   optionally substituted C₄-C₆alkyl;    -   C₁-C₆alkylthio, optionally substituted by one to three        substituents independently selected from the group consisting of        —NH₂, —OH, —NO₂, —CN, —SH, CO₂C₁-C₄alkyl, —CONH₂, SF₅, —SO₂NH₂,        C₁-C₄alkyl, C₃-C₄cycloalkyl, C₂-C₄alkenyl, C₅-C₆cycloalkenyl,        C₂-C₄alkynyl, —NH(C₁-C₆alkyl), —N(C₁-C₆alkyl)₂,        N—C₁-C₄alkanoylamino, C₁-C₄alkoxy, C₁-C₄haloalkoxy,        C₂-C₄alkenyloxy, C₂-C₄alkynyloxy, C₃-C₄cycloalkoxy,        C₅-C₆cycloalkenyloxy, C₁-C₄alkoxycarbonyl,        C₂-C₄alkenyloxycarbonyl, C₂-C₄alkynyloxycarbonyl, C₆—, C₁₀—,        C₁₄-aryloxycarbonyl, C₁-C₄alkanoyl, C₂-C₄alkenylcarbonyl,        C₂-C₄alkynylcarbonyl, C₆—, C₁₀—, C₁₄-arylcarbonyl,        C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₃-C₄cycloalkylthio,        C₂-C₄alkenylthio, C₅-C₆cycloalkenylthio, C₂-C₄alkynylthio,        C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, C₁-C₄alkylsulfonyl,        C₁-C₄haloalkylsulfonyl, —SO₂—NH(C₁-C₆alkyl),        —SO₂—N(C₁-C₆alkyl)₂, C₁-C₄alkylphosphinyl, C₁-C₄alkylphosphonyl,        N—C₁-C₄alkylaminocarbonyl, N,N-di-C₁-C₄alkylaminocarbonyl,        N—C₁-C₄alkanoylaminocarbonyl,        N—C₁-C₄alkanoyl-N—C₁-C₄alkylaminocarbonyl, C₆—, C₁₀—, C₁₄-aryl,        C₆—, C₁₀—, C₁₄-aryloxy, benzyl, benzyloxy, benzylthio, C₆—,        C₁₀—, C₁₄-arylthio, C₆—, C₁₀—, C₁₄-arylamino, benzylamino,        heterocyclyl, heteroaryl and trialkylsilyl, substituents bonded        via a double bond, such as C₁-C₄alkylidene (e.g. methylidene or        ethylidene), an oxo group, an imino group and a substituted        imino group;    -   and in each case optionally substituted C₄-C₆haloalkylthio,        C₄-C₆haloalkoxy, C₄-C₆alkoxy, C₄-C₆haloalkyl, C₃-C₆cycloalkyl,        C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₃-C₆cycloalkylsulfanyl,        C₃-C₆cycloalkylsulfinyl, C₃-C₆cycloalkylsulfonyl,        C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl,        C₂-C₆alkenylsulfanyl, C₂-C₆alkenylsulfinyl,        C₂-C₆alkenylsulfonyl, C₂-C₆alkinylsulfanyl,        C₂-C₆alkinylsulfinyl, C₂-C₆alkinylsulfonyl, phenylsulfanyl,        phenylsulfinyl, phenylsulfonyl, heterocyclylsulfanyl,        heterocyclylsulfinyl, heterocyclylsulfonyl, heteroarylsulfanyl,        heteroarylsulfinyl, heteroarylsulfonyl,        S—C₁-C₆alkylsulfinimidoyl, S—C₃-C₆cycloalkylsulfinimidoyl,        S—C₂-C₆alkenylsulfinimidoyl, S—C₂-C₆alkinylsulfinimidoyl,        S-phenylsulfinimidoyl, S-heterocyclylsulfinimidoyl,        S-heteroarylsulfinimidoyl, S—C₁-C₆alkylsulfonimidoyl,        S—C₃-C₆cycloalkylsulfonimidoyl, S—C₂-C₆alkenylsulfonimidoyl,        S—C₂-C₆alkinylsulfonimidoyl, S-phenylsulfonimidoyl,        S-heterocyclylsulfonimidoyl, S-heteroarylsulfonimidoyl,        —NH(C₁-C₆alkyl), —N(C₁-C₆alkyl)₂, —NHCO—C₁-C₆alkyl,        —N(C₁-C₆alkyl)CO—C₁-C₆alkyl, —N(C₃-C₆cycloalkyl)CO—C₁-C₆alkyl,        —NHCO-phenyl, —N(C₁-C₆alkyl)CO-phenyl,        —N(C₃-C₆cycloalkyl)CO-phenyl, —NHCO—C₃-C₆cycloalkyl,        —N(C₁-C₆alkyl)CO—(C₃-C₆cycloalkyl),        —N(C₃-C₆cycloalkyl)CO—(C₃-C₆cycloalkyl), —NHCO-heteroaryl,        —N(C₁-C₆alkyl)CO-heteroaryl, —N(C₃-C₆cycloalkyl)CO-heteroaryl,        —NHCO-heterocyclyl, —N(C₁-C₆alkyl)CO-heterocyclyl,        —N(C₃-C₆cycloalkyl)CO-heterocyclyl, —CO₂C₁-C₆alkyl,        —CONH(C₁-C₆alkyl), —CON(C₁-C₆alkyl)₂, —CONH(C₃-C₆cycloalkyl),        —CON(C₁-C₆alkyl)(C₃-C₆cycloalkyl), —CON(C₃-C₆cycloalkyl)₂,        —CONH-phenyl, —CON(C₁-C₆alkyl)phenyl,        —CON(C₃-C₆cycloalkyl)phenyl, —CONH-heteroaryl,        —CON(C₁-C₆alkyl)heteroaryl, —CON(C₃-C₆cycloalkyl)heteroaryl,        —CONH-heterocyclyl, —CON(C₁-C₆alkyl)heterocyclyl,        —CON(C₃-C₆cycloalkyl)heterocyclyl, —C(═NOC₁-C₆alkyl)H,        —C(═NOC₁-C₆alkyl)-C₁-C₆alkyl, —NHSO₂—C₁-C₆alkyl,        —N(C₁-C₆alkyl)SO₂—C₁-C₆alkyl, —N(C₃-C₆cycloalkyl)SO₂—C₁-C₆alkyl,        —NHSO₂-phenyl, —N(C₁-C₆alkyl)SO₂-phenyl,        —N(C₃-C₆cycloalkyl)SO₂-phenyl, —NHSO₂—C₃-C₆cycloalkyl,        —N(C₁-C₆alkyl)SO₂—(C₃-C₆cycloalkyl),        —N(C₃-C₆cycloalkyl)SO₂—(C₃-C₆cycloalkyl), —NHSO₂-heterocyclyl,        —N(C₁-C₄alkyl)SO₂-heterocyclyl,        —N(C₃-C₆cycloalkyl)SO₂-heterocyclyl, —NHSO₂-heteroaryl,        —N(C₁-C₆alkyl)SO₂-heteroaryl, —N(C₃-C₆cycloalkyl)SO₂-heteroaryl,        —SO₂NH(C₁-C₆alkyl), —SO₂N(C₁-C₆alkyl)₂,        —SO₂N(C₁-C₆alkyl)(C₃-C₆cycloalkyl), —SO₂NH(C₃-C₆cycloalkyl),        —SO₂N(C₃-C₆cycloalkyl)₂, —SO₂NH(phenyl),        —SO₂N(C₁-C₆alkyl)(phenyl), —SO₂N(C₁-C₄cycloalkyl)(phenyl),        —SO₂NH(heteroaryl), —SO₂N(C₁-C₆alkyl)(heteroaryl),        —SO₂N(C₃-C₆cycloalkyl)(heteroaryl), —SO₂NH(heterocyclyl),        —SO₂N(C₁-C₄alkyl)(heterocyclyl),        —SO₂N(C₃-C₆cycloalkyl)(heterocyclyl);    -   and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl        or 5- to 6-membered heteroaryl is optionally substituted with        one to two substituents, each independently selected from the        group consisting of halogen, —CN, in each case optionally        substituted C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy and        C₁-C₆haloalkoxy;    -   and an optionally substituted 4- to 6-membered saturated or        partially unsaturated heterocyclic ring;    -   and —SO₂NH₂;    -   and the other one to two optional substituent(s) are each        independently selected from group B consisting of    -   halogen, hydroxy, —NH₂, —CN, —SF₅, —COOH, —CONH₂, —NO₂,    -   and in each case optionally substituted C₁-C₆alkyl,        C₃-C₆cycloalkyl, C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₆haloalkyl,        C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio,        C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio,        C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, phenylsulfanyl,        phenylsulfinyl, phenylsulfonyl, —NH(C₁-C₆alkyl),        —N(C₁-C₆alkyl)₂, —NHCO—C₁-C₆alkyl, —N(C₁-C₆alkyl)CO—C₁-C₆alkyl,        —NHCO-phenyl, —CO₂C₁-C₆alkyl, —CONH(C₁-C₆alkyl),        —CON(C₁-C₆alkyl)₂, —CONH(C₃-C₆cycloalkyl),        —CON(C₁-C₆alkyl)(C₃-C₆cycloalkyl), —C(═NOC₁-C₆alkyl)H,        —C(═NOC₁-C₆alkyl)-C₁-C₆alkyl;    -   and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl        or 5- to 6-membered heteroaryl is optionally substituted with        one to two substituents, each independently selected from the        group consisting of halogen, —CN, in each case optionally        substituted C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy;    -   or-   R² is naphthyl optionally substituted by one to three substituents    independently selected from the group consisting of    -   halogen, hydroxy, —CN, —COOH, —CONH₂, —NO₂, —SF₅, —NH₂,    -   and in each case optionally substituted C₁-C₆alkyl,        C₃-C₆cycloalkyl, C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₆haloalkyl,        C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio,        C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₃-C₆cycloalkylsulfanyl,        C₃-C₆cycloalkylsulfinyl, C₃-C₆cycloalkylsulfonyl,        C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl,        C₁-C₆haloalkylsulfonyl, phenylsulfanyl, phenylsulfinyl,        phenylsulfonyl, —NH(C₁-C₆alkyl), —N(C₁-C₆alkyl)₂,        —NHCO—C₁-C₆alkyl, —N(C₁-C₆alkyl)CO—C₁-C₆alkyl, —NHCO-phenyl,        —CO₂C₁-C₆alkyl, —CONH(C₁-C₆alkyl), —CON(C₁-C₆alkyl)₂,        —C(═NOC₁-C₆alkyl)H, —C(═NOC₁-C₆alkyl)-C₁-C₆alkyl;    -   and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl        or 5- to 6-membered heteroaryl is optionally substituted with        one to two substituents, each independently selected from the        group consisting of halogen, —CN, in each case optionally        substituted C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy;    -   or-   R² is a heterocyclic ring which is selected from the group    consisting of 4- to 10-membered saturated and partially unsaturated    heterocyclyl, 5-membered heteroaryl, 9-membered heteroaryl and    10-membered heteroaryl, each of which is optionally substituted by    one to three substituents independently selected from the group    consisting of    -   halogen, ═O (oxo), hydroxy, —CN, —COOH, —CONH₂, —NO₂, —SF₅,        —NH₂, and in each case optionally substituted C₁-C₆alkyl,        C₃-C₆cycloalkyl, C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₆haloalkyl,        C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio,        C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₃-C₆cycloalkylsulfanyl,        C₃-C₆cycloalkylsulfinyl, C₃-C₆cycloalkylsulfonyl,        C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl,        C₁-C₆haloalkylsulfonyl, phenylsulfanyl, phenylsulfinyl,        phenylsulfonyl, —NH(C₁-C₆alkyl), —N(C₁-C₆alkyl)₂,        —NHCO—C₁-C₆alkyl, —N(C₁-C₆alkyl)CO—C₁-C₆alkyl, —NHCO-phenyl,        —CO₂C₁-C₆alkyl, —CONH(C₁-C₆alkyl), —CON(C₁-C₆alkyl)₂,        —C(═NOC₁-C₆alkyl)H, —C(═NOC₁-C₆alkyl)-C₁-C₆alkyl;    -   and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl        or 5- to 6-membered heteroaryl is optionally substituted with        one to two substituents, each independently selected from the        group consisting of halogen, —CN, in each case optionally        substituted C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy;    -   or-   R² is in each case optionally substituted C₁-C₆alkyl,    C₃-C₆cycloalkyl or C₁-C₆haloalkyl;-   R^(3a), R^(3b) are independently selected from the group consisting    of hydrogen; halogen; —CN; C₁-C₆alkyl optionally substituted by one    to three substituents independently selected from the group    consisting of halogen, hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, in    each case optionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl,    C₁-C₆alkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,    —NH(C₁-C₆alkyl), —N(C₁-C₆alkyl)₂, —NHCO—C₁-C₆alkyl,    —N(C₁-C₆alkyl)CO—C₁-C₆alkyl, —CO₂C₁-C₆alkyl, —CONH(C₁-C₆alkyl), and    —CON(C₁-C₆alkyl)₂; optionally substituted C₃-C₆cycloalkyl;    optionally substituted C₁-C₆haloalkyl; optionally substituted    C₂-C₆alkenyl; optionally substituted C₂-C₆haloalkenyl; optionally    substituted C₂-C₆alkynyl; benzyl wherein the phenyl substituent is    optionally substituted with one to five substituents, each    independently selected from the group consisting of halogen,    hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, —SF₅, in each case    optionally substituted C₁-C₆alkyl, C₁-C₆alkoxy, C₁-C₆alkylthio,    C₁-C₆alkylsulfinyl, and C₁-C₆alkylsulfonyl; heterocyclyl-C₁-C₆alkyl    wherein the heterocyclyl substituent is selected from the group    consisting of 4- to 10-membered saturated and partially unsaturated    heterocyclyl, 5-membered heteroaryl and 6-membered heteroaryl, each    of which is optionally substituted by one to three substituents    independently selected from the group consisting of halogen, ═O    (oxo), hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, in each case    optionally substituted C₁-C₆alkyl, and C₁-C₆alkoxy; phenyl    optionally substituted with one to five substituents, each    independently selected from the group consisting of halogen,    hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, —SF₅, in each case    optionally substituted C₁-C₆alkyl, C₁-C₆alkoxy, C₁-C₆alkylthio,    C₁-C₆alkylsulfinyl, and C₁-C₆alkylsulfonyl; or heterocyclyl wherein    the heterocyclyl substituent is selected from the group consisting    of 4- to 10-membered saturated and partially unsaturated    heterocyclyl, 5-membered heteroaryl and 6-membered heteroaryl, each    of which is optionally substituted by one to three substituents    independently selected from the group consisting of halogen, ═O    (oxo), hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, in each case    optionally substituted C₁-C₆alkyl, and C₁-C₆alkoxy;    -   or-   R^(3a), R^(3b) form together with the carbon to which they are    connected a C₃-C₆-carbocyclic or 3- to 6-membered heterocyclic ring    system, optionally substituted with one to two substituents, each    independently selected from the group consisting of halogen, —CN, in    each case optionally substituted C₁-C₆alkyl, C₁-C₆alkoxy and    C₁-C₆haloalkoxy;-   R⁴ is pyridine, pyrimidine, pyrazine, pyridazine or 5-membered    heteroaryl, wherein the pyridine, pyrimidine, pyrazine, pyridazine    or 5-membered heteroaryl is optionally substituted with one to three    substituents selected from the group consisting of halogen, hydroxy,    —CN, —COOH, —CO₂—C₁-C₆alkyl, —SO₂NH₂, —CONH₂, —CSNH₂, —NO₂, —NH₂, in    each case optionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl,    C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio,    C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio,    C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl,    C₃-C₆cycloalkylsulfanyl, C₃-C₆cycloalkylsulfinyl,    C₃-C₆cycloalkylsulfonyl, C₂-C₄alkenylsulfanyl, C₂-C₄alkenylsulfinyl,    C₂-C₄alkenylsulfonyl, C₂-C₄alkinylsulfanyl, C₂-C₄alkinylsulfinyl,    C₂-C₄alkinylsulfonyl, phenylsulfanyl, phenylsulfinyl,    phenylsulfonyl, S—C₁-C₆alkylsulfinimidoyl,    S—C₃-C₆cycloalkylsulfinimidoyl, S—C₂-C₆alkenylsulfinimidoyl,    S—C₂-C₆alkinylsulfinimidoyl, S-phenylsulfinimidoyl,    S—C₁-C₆alkylsulfonimidoyl, S—C₃-C₆cycloalkylsulfonimidoyl,    S—C₂-C₆alkenylsulfonimidoyl, S—C₂-C₆alkinylsulfonimidoyl,    S-phenylsulfonimidoyl, —NH(C₁-C₆alkyl), —N(C₁-C₆alkyl)₂,    —NHCO—C₁-C₆alkyl, —N(C₁-C₆alkyl)CO—C₁-C₆alkyl,    —N(C₃-C₆cycloalkyl)CO—C₁-C₆alkyl, —NHCO—C₃-C₆cycloalkyl,    —N(C₁-C₆alkyl)CO—(C₃-C₆cycloalkyl),    —N(C₃-C₆cycloalkyl)CO—(C₃-C₆cycloalkyl), —N(C₁-C₆alkyl)CO-phenyl,    —N(C₃-C₆cycloalkyl)CO-phenyl, —NHCO-phenyl, —N(CO—C₁-C₆alkyl)₂,    —N(CO—C₃-C₆cycloalkyl)₂, —N(CO-phenyl)₂,    —N(CO—C₃-C₆cycloalkyl)(CO—C₁-C₆alkyl),    —N(CO—C₃-C₆cycloalkyl)(CO-phenyl), —N(CO—C₁-C₆alkyl)(CO-phenyl),    —CONH(C₁-C₆alkyl), —CON(C₁-C₆alkyl)₂, —CONH(C₃-C₆cycloalkyl),    —CON(C₁-C₆alkyl)(C₃-C₆cycloalkyl), —CON(C₃-C₆cycloalkyl)₂,    —CONH—SO₂—C₁-C₆alkyl, —CONH—SO₂-phenyl, —CONH—SO₂—(C₃-C₆cycloalkyl),    —CON(C₁-C₆alkyl)-SO₂—C₁-C₆alkyl, —CON(C₁-C₆alkyl)-SO₂-phenyl,    —CON(C₁-C₆alkyl)-SO₂—(C₃-C₆cycloalkyl), —CONH-phenyl,    —CON(C₁-C₆alkyl)phenyl, —CON(C₃-C₆cycloalkyl)phenyl,    —N(SO₂C₁-C₆alkyl)₂, —N(SO₂C₁-C₆haloalkyl)₂, —N(SO₂C₃-C₆cycloalkyl)₂,    —N(SO₂C₁-C₆alkyl)SO₂-phenyl, —N(SO₂C₃-C₆cycloalkyl)SO₂-phenyl,    —NHSO₂—C₁-C₆alkyl, —NHSO₂—C₁-C₆haloalkyl,    —N(C₁-C₆alkyl)SO₂—C₁-C₆alkyl, —N(C₃-C₆cycloalkyl)SO₂—C₁-C₆alkyl,    —NHSO₂-phenyl, —N(C₁-C₆alkyl)SO₂-phenyl,    —N(C₃-C₆cycloalkyl)SO₂-phenyl, —NHSO₂—C₃-C₆cycloalkyl,    —N(C₁-C₆alkyl)SO₂—(C₃-C₆cycloalkyl),    —N(C₃-C₆cycloalkyl)SO₂—(C₃-C₆cycloalkyl), —SO₂NH(C₁-C₆alkyl),    —SO₂N(C₁-C₆alkyl)₂, —SO₂N(C₁-C₆alkyl)(C₃-C₆cycloalkyl),    —SO₂NH(C₃-C₆cycloalkyl), —SO₂N(C₃-C₆cycloalkyl)₂, —SO₂NH(phenyl),    —SO₂N(C₁-C₆alkyl)(phenyl), —SO₂N(C₁-C₄cycloalkyl)(phenyl),    —C(═NOC₁-C₆alkyl)H and —C(═NOC₁-C₆alkyl)-C₁-C₆alkyl;-   R⁵ is hydrogen, halogen, —CN, or in each case optionally substituted    C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆alkoxyC(O)—,    (C₁-C₆alkoxy)₂CH—, —CO₂C₁-C₆alkyl, —CONH(C₁-C₆alkyl),    —CON(C₁-C₆alkyl)₂, —NHCO—C₁-C₆alkyl, —N(C₁-C₆alkyl)CO—C₁-C₆alkyl,    —C(═NOC₁-C₆alkyl)H, or —C(═NOC₁-C₆alkyl)-C₁-C₆alkyl.

The compounds of the formula (I) likewise encompass any diastereomers orenantiomers and E/Z isomers which exist, and also salts and N-oxides ofcompounds of the formula (I), and the use thereof for control of animalpests.

Preferred radical definitions for the formulae specified above andhereinafter are given below.

Preference (Configuration 2-1) is given to the compounds of the formula(I) in which

-   X is O or S;-   Q¹ and Q² are independently CR⁵ or N, provided at least one of Q¹    and Q² is N; Y is a direct bond or CH₂;-   R¹ is hydrogen; C₁-C₆alkyl optionally substituted with one    substituent selected from —CN, —CONH₂, —COOH, —NO₂ and —Si(CH₃)₃;    C₁-C₆haloalkyl; C₂-C₆alkenyl; C₂-C₆haloalkenyl; C₂-C₆alkynyl;    C₂-C₆haloalkynyl; C₃-C₄cycloalkyl-C₁-C₂alkyl- wherein the    C₃-C₄cycloalkyl is optionally substituted with one or two halogen    atoms; oxetan-3-yl-CH₂—; or benzyl optionally substituted with    halogen or C₁-C₃haloalkyl;-   R² is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein    the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is    substituted with one to five substituents, provided at least one    substituent is on either carbon adjacent to the carbon bonded to the    C═X group, each independently selected from the group consisting of    halogen, hydroxy, —NH₂, —CN, —SF₅, —COOH, —CONH₂, —NO₂, C₁-C₆alkyl,    optionally substituted C₃-C₆cycloalkyl; C₃-C₆cycloalkyl-C₁-C₆alkyl,    C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₃haloalkoxy, C₁-C₆alkylthio,    C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₃-C₆cycloalkylsulfanyl,    C₃-C₆cycloalkylsulfinyl, C₃-C₆cycloalkylsulfonyl,    C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl;    phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, wherein in each case    the phenyl is optionally substituted with one to two substituents    selected from the group consisting of halogen, CN, C₁-C₆alkyl and    C₁-C₃haloalkyl; —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl,    —N(C₁-C₄alkyl)CO—C₁-C₄alkyl; —NHCO-phenyl, wherein the phenyl is    optionally substituted with one to two substituents selected from    the group consisting of halogen, CN, C₁-C₆alkyl and C₁-C₃haloalkyl;    —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂,    —CONH(C₃-C₆cycloalkyl), —CON(C₁-C₄alkyl)(C₃-C₆cycloalkyl),    —C(═NOC₁-C₄alkyl)H, —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl; phenyl and 5- to    6-membered heteroaryl, wherein the phenyl or 5- to 6-membered    heteroaryl is optionally substituted with one to two substituents,    each independently selected from the group consisting of halogen,    —CN, C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy;    -   or-   R² is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein    the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is    substituted with a total of one to three substituents, provided the    substituent(s) are not on either carbon adjacent to the carbon    bonded to the C═X group and at least one and up to three    substituent(s) are independently selected from group A consisting of    C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,    C₃-C₆cycloalkylsulfanyl, C₃-C₆cycloalkylsulfinyl,    C₃-C₆cycloalkylsulfonyl, C₁-C₃haloalkylsulfinyl,    C₁-C₃haloalkylsulfonyl; phenylsulfanyl, phenylsulfinyl,    phenylsulfonyl, wherein in each case the phenyl is optionally    substituted with one to two substituents selected from the group    consisting of halogen, —CN, C₁-C₆alkyl and C₁-C₃haloalkyl;    optionally substituted C₃-C₆cycloalkyl; —NH(C₁-C₄alkyl),    —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl, —N(C₁-C₄alkyl)CO—C₁-C₄alkyl;    —NHCO-phenyl, wherein the phenyl is optionally substituted with one    to two substituents selected from the group consisting of halogen,    CN, C₁-C₆alkyl and C₁-C₃haloalkyl; —CO₂C₁-C₄alkyl,    —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂, —CONH(C₃-C₆cycloalkyl),    —CON(C₁-C₄alkyl)(C₃-C₆cycloalkyl), —C(═NOC₁-C₄alkyl)H,    —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl; phenyl and 5- to 6-membered    heteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl is    optionally substituted with one to two substituents, each    independently selected from the group consisting of halogen, —CN,    C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy and C₁-C₄haloalkoxy; the    other one to two optional substituent(s) are each independently    selected from group B consisting of halogen, hydroxy, —NH₂, —CN,    —SF₅, —COH, —CONH₂, —NO₂, C₁-C₆alkyl, optionally substituted    C₃-C₆cycloalkyl; C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₃haloalkyl,    C₁-C₄alkoxy, C₁-C₃haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,    C₁-C₆alkylsulfonyl, C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl,    C₁-C₃haloalkylsulfonyl; phenylsulfanyl, phenylsulfinyl,    phenylsulfonyl, wherein in each case the phenyl is optionally    substituted with one to two substituents selected from the group    consisting of halogen, CN, C₁-C₆alkyl and C₁-C₃haloalkyl;    —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl,    —N(C₁-C₄alkyl)CO—C₁-C₄alkyl; —NHCO-phenyl, wherein the phenyl is    optionally substituted with one to two substituents selected from    the group consisting of halogen, CN, C₁-C₆alkyl and C₁-C₃haloalkyl;    —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂,    —CONH(C₃-C₆cycloalkyl), —CON(C₁-C₄alkyl)(C₃-C₆cycloalkyl),    —C(═NOC₁-C₄alkyl)H, —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl; phenyl and 5- to    6-membered heteroaryl, wherein the phenyl or 5- to 6-membered    heteroaryl is optionally substituted with one to two substituents,    each independently selected from the group consisting of halogen,    —CN, C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy;    -   or-   R² is naphthyl optionally substituted by one to three substituents    independently selected from the group consisting of halogen,    hydroxy, —CN, —COH, —CONH₂, —NO₂, —SF₅, —NH₂, C₁-C₆alkyl, optionally    substituted C₃-C₆cycloalkyl; C₃-C₆cycloalkyl-C₁-C₆alkyl,    C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₃haloalkoxy, C₁-C₆alkylthio,    C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₃-C₆cycloalkylsulfanyl,    C₃-C₆cycloalkylsulfinyl, C₃-C₆cycloalkylsulfonyl,    C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl;    phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, wherein in each case    the phenyl is optionally substituted with one to two substituents    selected from the group consisting of halogen, CN, C₁-C₆alkyl and    C₁-C₃haloalkyl; —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl,    —N(C₁-C₄alkyl)CO—C₁-C₄alkyl; —NHCO-phenyl, wherein the phenyl is    optionally substituted with one to two substituents selected from    the group consisting of halogen, CN, C₁-C₆alkyl and C₁-C₃haloalkyl;    —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂,    —C(═NOC₁-C₄alkyl)H, —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl; phenyl and 5- to    6-membered heteroaryl, wherein the phenyl or 5- to 6-membered    heteroaryl is optionally substituted with one to two substituents,    each independently selected from the group consisting of halogen,    —CN, C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy;    -   or-   R² is a heterocyclic ring which is selected from the group    consisting of 4- to 10-membered saturated and partially unsaturated    heterocyclyl, 5-membered heteroaryl, 9-membered heteroaryl and    10-membered heteroaryl, each of which is optionally substituted by    one to three substituents independently selected from the group    consisting of halogen, ═O (oxo), hydroxy, —CN, —COOH, —CONH₂, —NO₂,    —SF₅, —NH₂, C₁-C₆alkyl, optionally substituted C₃-C₆cycloalkyl;    C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy,    C₁-C₃haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,    C₁-C₆alkylsulfonyl, C₃-C₆cycloalkylsulfanyl,    C₃-C₆cycloalkylsulfinyl, C₃-C₆cycloalkylsulfonyl,    C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl;    phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, wherein in each case    the phenyl is optionally substituted with one to two substituents    selected from the group consisting of halogen, CN, C₁-C₆alkyl and    C₁-C₃haloalkyl; —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl,    —N(C₁-C₄alkyl)CO—C₁-C₄alkyl; —NHCO-phenyl, wherein the phenyl is    optionally substituted with one to two substituents selected from    the group consisting of halogen, CN, C₁-C₆alkyl and C₁-C₃haloalkyl;    —C₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂,    —C(═NOC₁-C₄alkyl)H, —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl; phenyl and 5- to    6-membered heteroaryl, wherein the phenyl or 5- to 6-membered    heteroaryl is optionally substituted with one to two substituents,    each independently selected from the group consisting of halogen,    —CN, C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy;    -   or-   R² is C₁-C₆alkyl substituted with one substituent selected from the    group consisting of C₁-C₃alkoxy-, C₁-C₃haloalkoxy-, C₁-C₆alkylthio,    C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₃haloalkylthio,    C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl; phenyl and 5- to    6-membered heteroaryl, wherein the phenyl or 5- to 6-membered    heteroaryl is optionally substituted with one to two substituents,    each independently selected from the group consisting of halogen,    —CN, C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy; C₃-C₆cycloalkyl    optionally substituted with one to two substituents selected from    the group consisting of halogen, —CN, —COOH, —CONH₂, C₁-C₆alkyl,    C₁-C₆haloalkyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy, —CO₂C₁-C₄alkyl,    —CONH(C₁-C₄alkyl), and —CON(C₁-C₄alkyl)₂; C₁-C₆haloalkyl;-   R^(3a), R^(3b) are independently selected from the group consisting    of hydrogen; halogen: —CN; C₁-C₆alkyl optionally substituted by one    to three substituents independently selected from the group    consisting of hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, C₁-C₆alkyl,    C₃-C₆cycloalkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₃haloalkoxy,    C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,    C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl,    —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl), —NHCO—C₁-C₄alkyl,    —N(C₁-C₄alkyl)CO—C₁-C₄alkyl, —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), and    —CON(C₁-C₄alkyl)₂; C₃-C₆cycloalkyl optionally substituted with one    to two substituents selected from the group consisting of halogen,    —CN, —COOH, —CONH₂, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl,    C₁-C₆alkoxy, C₁-C₆haloalkoxy, —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), and    —CON(C₁-C₄alkyl)₂; C₁-C₆haloalkyl optionally substituted with one to    two substituents selected from the group consisting of hydroxy, —CN,    C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, —CO₂C₁-C₄alkyl,    —CONH(C₁-C₄alkyl), and —CON(C₁-C₄alkyl)₂; C₂-C₆alkenyl;    C₂-C₆haloalkenyl; C₂-C₆alkynyl; C₂-C₆haloalkynyl; benzyl wherein the    phenyl substituent is optionally substituted with one to five    substituents, each independently selected from the group consisting    of halogen, hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, —SF₅,    C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy,    C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,    C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, and    C₁-C₃haloalkylsulfonyl; heterocyclyl-C₁-C₆alkyl wherein the    heterocyclyl substituent is selected from the group consisting of 4-    to 10-membered saturated and partially unsaturated heterocyclyl,    5-membered heteroaryl and 6-membered heteroaryl, each of which is    optionally substituted by one to three substituents independently    selected from the group consisting of halogen, ═O (oxo), hydroxy,    —CN, —COH, —CONH₂, —NO₂, —NH₂, C₁-C₆alkyl, C₁-C₃haloalkyl and    C₁-C₄alkoxy; phenyl optionally substituted with one to five    substituents, each independently selected from the group consisting    of halogen, hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, —SF₅,    C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy,    C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,    C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, and    C₁-C₃haloalkylsulfonyl; and heterocyclyl wherein the heterocyclyl    substituent is selected from the group consisting of 4- to    10-membered saturated and partially unsaturated heterocyclyl,    5-membered heteroaryl and 6-membered heteroaryl, each of which is    optionally substituted by one to three substituents independently    selected from the group consisting of halogen, ═O (oxo), hydroxy,    —CN, —COOH, —CONH₂, —NO₂, —NH₂, C₁-C₆alkyl, C₁-C₃haloalkyl and    C₁-C₄alkoxy;    -   or-   R^(3a), R^(3b) form together with the carbon to which they are    connected a C₃-C₆-carbocyclic or 3- to 6-membered heterocyclic ring    system, optionally substituted with one to two substituents, each    independently selected from the group consisting of halogen, —CN,    C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy and C₁-C₃haloalkoxy;-   R⁴ is pyridine, pyrimidine, pyrazine, pyridazine or 5-membered    heteroaryl, wherein the pyridine, pyrimidine, pyrazine, pyridazine    or 5-membered heteroaryl is optionally substituted with one to three    substituents selected from the group consisting of halogen, hydroxy,    —CN, —COOH, —CONH₂, —CSNH₂, —NO₂, —NH₂, C₁-C₆alkyl, C₃-C₆cycloalkyl,    C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₃haloalkoxy, C₁-C₆alkylthio,    C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₃haloalkylthio,    C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl, —NH(C₁-C₄alkyl),    —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl, —NHCO—C₃-C₆cycloalkyl;    —NHCO-phenyl, wherein the phenyl is optionally substituted with one    to two substituents selected from the group consisting of halogen,    CN, C₁-C₆alkyl and C₁-C₃haloalkyl; —N(C₁-C₄alkyl)CO—C₁-C₄alkyl,    —N(C₁-C₄alkyl)CO—C₃-C₆cycloalkyl; —N(C₁-C₄alkyl)CO-phenyl, wherein    the phenyl is optionally substituted with one to two substituents    selected from the group consisting of halogen, —CN, C₁-C₆alkyl and    C₁-C₃haloalkyl; —N(SO₂C₁-C₃alkyl)₂, —NH(SO₂C₁-C₃alkyl),    —N(C₁-C₄alkyl)(SO₂C₁-C₃alkyl), —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl),    —CON(C₁-C₄alkyl)₂, —C(═NOC₁-C₄alkyl)H, and    —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl;-   R⁵ is hydrogen, halogen, —CN, C₁-C₃alkyl, C₁-C₃haloalkyl,    C₃-C₄cycloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkoxyC(O)—,    (C₁-C₃alkoxy)₂CH—, —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl),    —CON(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl, —N(C₁-C₄alkyl)CO—C₁-C₄alkyl,    —C(═NOC₁-C₄alkyl)H, or —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl.

Also preferred (Configuration 2-2) are the compounds of the formula (I)in which

-   X is O or S;-   Q¹ and Q² are independently CR⁵ or N, provided at least one of Q¹    and Q² is N;-   Y is a direct bond or CH₂;-   R¹ is hydrogen; C₁-C₆alkyl optionally substituted with one    substituent selected from —CN, —CONH₂, —COOH, —NO₂ and —Si(CH₃)₃;    C₁-C₆haloalkyl; C₂-C₆alkenyl; C₂-C₆haloalkenyl; C₂-C₆alkynyl;    C₂-C₆haloalkynyl; C₃-C₄cycloalkyl-C₁-C₂alkyl- wherein the    C₃-C₄cycloalkyl is optionally substituted with one or two halogen    atoms; oxetan-3-yl-CH₂—; or benzyl optionally substituted with    halogen or C₁-C₃haloalkyl;-   R² is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein    the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is    substituted with one to five substituents, provided at least one    substituent is on either carbon adjacent to the carbon bonded to the    C═X group, each independently selected from the group consisting of    -   halogen, hydroxy, —NH₂, —CN, —SF₅, —COOH, —CONH₂, —NO₂,        C₁-C₆alkyl,    -   optionally substituted C₃-C₆cycloalkyl;        C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy,        C₁-C₃haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,        C₁-C₆alkylsulfonyl, C₃-C₆cycloalkylsulfanyl,        C₃-C₆cycloalkylsulfinyl, C₃-C₆cycloalkylsulfonyl,        C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl,        C₁-C₃haloalkylsulfonyl;    -   phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, wherein in each        case the phenyl is optionally substituted with one to two        substituents selected from the group consisting of halogen, CN,        C₁-C₆alkyl and C₁-C₃haloalkyl;    -   —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl,        —N(C₁-C₄alkyl)CO—C₁-C₄alkyl;    -   —NHCO-phenyl, wherein the phenyl is optionally substituted with        one to two substituents selected from the group consisting of        halogen, CN, C₁-C₆alkyl and C₁-C₃haloalkyl;    -   —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂,        —CONH(C₃-C₆cycloalkyl), —CON(C₁-C₄alkyl)(C₃-C₆cycloalkyl),        —C(═NOC₁-C₄alkyl)H, —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl;    -   and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl        or 5- to 6-membered heteroaryl is optionally substituted with        one to two substituents, each independently selected from the        group consisting of halogen, —CN, C₁-C₆alkyl, C₁-C₃haloalkyl and        C₁-C₄alkoxy;    -   or-   R² is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein    the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is    substituted with a total of one to three substituents, provided the    substituent(s) are not on either carbon adjacent to the carbon    bonded to the C═X group and at least one and up to three    substituent(s) are independently selected from group A consisting of    -   C₄-C₆-alkyl, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,        C₁-C₆alkylsulfonyl, C₃-C₆cycloalkylsulfanyl,        C₃-C₆cycloalkylsulfinyl, C₃-C₆cycloalkylsulfonyl,        C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl;    -   phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, wherein in each        case the phenyl is optionally substituted with one to two        substituents selected from the group consisting of halogen, CN,        C₁-C₆alkyl and C₁-C₃haloalkyl;    -   optionally substituted C₃-C₆cycloalkyl;    -   —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl,        —N(C₁-C₄alkyl)CO—C₁-C₄alkyl, —NHCO—C₃-C₄cycloalkyl,        —NHSO₂-phenyl;    -   —NHCO-phenyl, wherein the phenyl is optionally substituted with        one to two substituents selected from the group consisting of        halogen, —CN, C₁-C₆alkyl and C₁-C₃haloalkyl;    -   —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂,        —CONH(C₃-C₆cycloalkyl), —CON(C₁-C₄alkyl)(C₃-C₆cycloalkyl),        —C(═NOC₁-C₄alkyl)H, —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl;    -   and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl        or 5- to 6-membered heteroaryl is optionally substituted with        one to two substituents, each independently selected from the        group consisting of halogen, —CN, C₁-C₆alkyl, C₁-C₃haloalkyl,        C₁-C₄alkoxy and C₁-C₄haloalkoxy;    -   and the other one to two optional substituent(s) are each        independently selected from group B consisting of    -   halogen, hydroxy, —NH₂, —CN, —SF₅, —COOH, —CONH₂, —NO₂,        C₁-C₆alkyl,    -   optionally substituted C₃-C₆cycloalkyl;    -   C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy,        C₁-C₃haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,        C₁-C₆alkylsulfonyl, C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl,        C₁-C₃haloalkylsulfonyl;    -   phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, wherein in each        case the phenyl is optionally substituted with one to two        substituents selected from the group consisting of halogen, CN,        C₁-C₆alkyl and C₁-C₃haloalkyl;    -   —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl,        —N(C₁-C₄alkyl)CO—C₁-C₄alkyl; —NHCO-phenyl, wherein the phenyl is        optionally substituted with one to two substituents selected        from the group consisting of halogen, CN, C₁-C₆alkyl and        C₁-C₃haloalkyl;    -   —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂,        —CONH(C₃-C₆cycloalkyl), —CON(C₁-C₄alkyl)(C₃-C₆cycloalkyl),        —C(═NOC₁-C₄alkyl)H, —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl;    -   and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl        or 5- to 6-membered heteroaryl is optionally substituted with        one to two substituents, each independently selected from the        group consisting of halogen, —CN, C₁-C₆alkyl, C₁-C₃haloalkyl and        C₁-C₄alkoxy;    -   or-   R² is naphthyl optionally substituted by one to three substituents    independently selected from the group consisting of    -   halogen, hydroxy, —CN, —COOH, —CONH₂, —NO₂, —SF₅, —NH₂,        C₁-C₆alkyl, optionally substituted C₃-C₆cycloalkyl;    -   C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy,        C₁-C₃haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,        C₁-C₆alkylsulfonyl, C₃-C₆cycloalkylsulfanyl,        C₃-C₆cycloalkylsulfinyl, C₃-C₆cycloalkylsulfonyl,        C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl,        C₁-C₃haloalkylsulfonyl;    -   phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, wherein in each        case the phenyl is optionally substituted with one to two        substituents selected from the group consisting of halogen, CN,        C₁-C₆alkyl and C₁-C₃haloalkyl;    -   —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl,        —N(C₁-C₄alkyl)CO—C₁-C₄alkyl; —NHCO-phenyl, wherein the phenyl is        optionally substituted with one to two substituents selected        from the group consisting of halogen, CN, C₁-C₆alkyl and        C₁-C₃haloalkyl;    -   —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂,        —C(═NOC₁-C₄alkyl)H, —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl;    -   and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl        or 5- to 6-membered heteroaryl is optionally substituted with        one to two substituents, each independently selected from the        group consisting of halogen, —CN, C₁-C₆alkyl, C₁-C₃haloalkyl and        C₁-C₄alkoxy;    -   or-   R² is a heterocyclic ring which is selected from the group    consisting of 4- to 10-membered saturated and partially unsaturated    heterocyclyl, 5-membered heteroaryl, 9-membered heteroaryl and    10-membered heteroaryl, each of which is optionally substituted by    one to three substituents independently selected from the group    consisting of    -   halogen, ═O (oxo), hydroxy, —CN, —COOH, —CONH₂, —NO₂, —SF₅,        —NH₂, C₁-C₆alkyl,    -   optionally substituted C₃-C₆cycloalkyl;    -   C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy,        C₁-C₃haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,        C₁-C₆alkylsulfonyl, C₃-C₆cycloalkylsulfanyl,        C₃-C₆cycloalkylsulfinyl, C₃-C₆cycloalkylsulfonyl,        C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl,        C₁-C₃haloalkylsulfonyl;    -   phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, wherein in each        case the phenyl is optionally substituted with one to two        substituents selected from the group consisting of halogen, CN,        C₁-C₆alkyl and C₁-C₃haloalkyl;    -   —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl,        —N(C₁-C₄alkyl)CO—C₁-C₄alkyl; —NHCO-phenyl, wherein the phenyl is        optionally substituted with one to two substituents selected        from the group consisting of halogen, CN, C₁-C₆alkyl and        C₁-C₃haloalkyl;    -   —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂,        —C(═NOC₁-C₄alkyl)H, —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl;    -   and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl        or 5- to 6-membered heteroaryl is optionally substituted with        one to two substituents, each independently selected from the        group consisting of halogen, —CN, C₁-C₆alkyl, C₁-C₃haloalkyl and        C₁-C₄alkoxy;    -   or-   R² is C₁-C₆alkyl substituted with one substituent selected from the    group consisting of    -   C₁-C₃alkoxy-, C₁-C₃haloalkoxy-, C₁-C₆alkylthio,        C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₃haloalkylthio,        C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl;    -   phenyl and 5- to 6-membered heteroaryl, wherein the phenyl or 5-        to 6-membered heteroaryl is optionally substituted with one to        two substituents, each independently selected from the group        consisting of halogen, —CN, C₁-C₆alkyl, C₁-C₃haloalkyl and        C₁-C₄alkoxy;    -   C₃-C₆cycloalkyl optionally substituted with one to two        substituents selected from the group consisting of halogen, —CN,        —COH, —CONH₂, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl,        C₁-C₆alkoxy, —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), and        —CON(C₁-C₄alkyl);    -   and C₁-C₆haloalkyl;-   R^(3a), R^(3b) are independently selected from the group consisting    of hydrogen; halogen; —CN; C₁-C₆alkyl optionally substituted by one    to three substituents independently selected from the group    consisting of hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, C₁-C₆alkyl,    C₃-C₆cycloalkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₃haloalkoxy,    C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,    C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl,    —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl,    —N(C₁-C₄alkyl)CO—C₁-C₄alkyl, —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), and    —CON(C₁-C₄alkyl)₂; C₃-C₆cycloalkyl optionally substituted with one    to two substituents selected from the group consisting of halogen,    —CN, —COOH, —CONH₂, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl,    C₁-C₆alkoxy, C₁-C₆haloalkoxy, —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), and    —CON(C₁-C₄alkyl)₂; C₁-C₆haloalkyl optionally substituted with one to    two substituents selected from the group consisting of hydroxy, —CN,    C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, —CO₂C₁-C₄alkyl,    —CONH(C₁-C₄alkyl), and —CON(C₁-C₄alkyl)₂; C₂-C₆alkenyl;    C₂-C₆haloalkenyl; C₂-C₆alkynyl; C₂-C₆haloalkynyl; benzyl wherein the    phenyl substituent is optionally substituted with one to five    substituents, each independently selected from the group consisting    of halogen, hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, —SF₅,    C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy,    C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,    C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, and    C₁-C₃haloalkylsulfonyl; heterocyclyl-C₁-C₆alkyl wherein the    heterocyclyl substituent is selected from the group consisting of 4-    to 10-membered saturated and partially unsaturated heterocyclyl,    5-membered heteroaryl and 6-membered heteroaryl, each of which is    optionally substituted by one to three substituents independently    selected from the group consisting of halogen, ═O (oxo), hydroxy,    —CN, —COH, —CONH₂, —NO₂, —NH₂, C₁-C₆alkyl, C₁-C₃haloalkyl and    C₁-C₄alkoxy; phenyl optionally substituted with one to five    substituents, each independently selected from the group consisting    of halogen, hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, —SF₅,    C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy,    C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,    C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, and    C₁-C₃haloalkylsulfonyl; and heterocyclyl wherein the heterocyclyl    substituent is selected from the group consisting of 4- to    10-membered saturated and partially unsaturated heterocyclyl,    5-membered heteroaryl and 6-membered heteroaryl, each of which is    optionally substituted by one to three substituents independently    selected from the group consisting of halogen, ═O (oxo), hydroxy,    —CN, —COOH, —CONH₂, —NO₂, —NH₂, C₁-C₆alkyl, C₁-C₃haloalkyl and    C₁-C₄alkoxy;    -   or-   R^(3a), R^(3b) form together with the carbon to which they are    connected a C₃-C₆-carbocyclic or 3- to 6-membered heterocyclic ring    system, optionally substituted with one to two substituents, each    independently selected from the group consisting of halogen, —CN,    C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy and C₁-C₃haloalkoxy;-   R⁴ is pyridine, pyrimidine, pyrazine, pyridazine or 5-membered    heteroaryl, wherein the pyridine, pyrimidine, pyrazine, pyridazine    or 5-membered heteroaryl is optionally substituted with one to three    substituents selected from the group consisting of halogen, hydroxy,    —CN, —COOH, —CO₂—C₁-C₆alkyl, —CONH₂, —CSNH₂, —NO₂, —NH₂, C₁-C₆alkyl,    C₃-C₆cycloalkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₃haloalkoxy,    C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,    C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl,    —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl, wherein the    alkyl is optionally substituted with —CN, C₁-C₆alkyl and    C₁-C₄alkoxy; —NHCO—C₁-C₄haloalkyl, —NHCO—C₃-C₆cycloalkyl, wherein    the cycloalkyl is optionally substituted with one to two    substituents selected from the group consisting of halogen, —CN,    C₁-C₆alkyl or C₁-C₄alkoxy; —NHCO-phenyl, wherein the phenyl is    optionally substituted with one to two substituents selected from    the group consisting of halogen, —CN, C₁-C₆alkyl and C₁-C₃haloalkyl;    —N(C₁-C₄alkyl)CO—C₁-C₄alkyl, —N(C₁-C₄alkyl)CO—C₃-C₆cycloalkyl;    —N(C₁-C₄alkyl)CO-phenyl, wherein the phenyl is optionally    substituted with one to two substituents selected from the group    consisting of halogen, CN, C₁-C₆alkyl and C₁-C₃haloalkyl;    —N(SO₂C₁-C₃alkyl)₂, —NH(SO₂C₁-C₃alkyl),    —N(C₁-C₄alkyl)(SO₂C₁-C₃alkyl), —N(SO₂C₁-C₃haloalkyl)₂,    —NH(SO₂C₁-C₃haloalkyl), —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂,    —CONH—SO₂—C₁-C₃alkyl, —CON(C₁-C₄alkyl)(C₃-C₆cycloalkyl),    —CONH(C₁-C₄haloalkyl), —CONH(C₃-C₆cycloalkyl),    —CONH(C₃-C₆cyanocycloalkyl), —C(═NOC₁-C₄alkyl)H and    —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl; and —CONH-phenyl, wherein the phenyl    is optionally substituted with one to two substituents, each    independently selected from the group consisting of halogen, —CN,    C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy;-   R⁵ is hydrogen, halogen, —CN, C₁-C₃alkyl, C₁-C₃haloalkyl,    C₃-C₄cycloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkoxyC(O)—,    (C₁-C₃alkoxy)₂CH—, —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl),    —CON(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl, —N(C₁-C₄alkyl)CO—C₁-C₄alkyl,    —C(═NOC₁-C₄alkyl)H, or —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl.

Further preferred (Configuration 3-1) are the compounds of the formula(I) in which

-   X is O or S;-   Q¹ and Q² are independently CR⁵ or N, provided at least one of Q¹    and Q² is N;-   Y is a direct bond or CH₂;-   R¹ is hydrogen; C₁-C₃alkyl optionally substituted with one    substituent selected from —CN, —CONH₂, —COOH, —NO₂ and —Si(CH₃)₃;    C₁-C₃haloalkyl; C₂-C₄alkenyl; C₂-C₄haloalkenyl; C₂-C₄alkynyl;    C₂-C₄haloalkynyl; C₃-C₄cycloalkyl-C₁-C₂alkyl- wherein the    C₃-C₄cycloalkyl is optionally substituted with one or two halogen    atoms; oxetan-3-yl-CH₂—; or benzyl optionally substituted with    halogen or C₁-C₃haloalkyl;-   R² is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein    the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is    substituted with one to five substituents, provided at least one    substituent is on either carbon adjacent to the carbon bonded to the    C═X group, each independently selected from the group consisting of    halogen, —CN, —NO₂, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₃haloalkyl,    C₁-C₄alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl,    C₁-C₃alkylsulfonyl, C₃-C₄cycloalkylsulfanyl,    C₃-C₄cycloalkylsulfinyl, C₃-C₄cycloalkylsulfonyl,    C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl;    phenyl and 5- to 6-membered heteroaryl, wherein the phenyl or 5- to    6-membered heteroaryl is optionally substituted with one to two    substituents selected from the group consisting of halogen, —CN,    C₁-C₃alkyl and C₁-C₃haloalkyl;    -   or-   R² is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein    the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is    substituted with a total of one to three substituents, provided the    substituent(s) are not on either carbon adjacent to the carbon    bonded to the C═X group and at least one and up to two    substituent(s) are independently selected from group A consisting of    C₃-C₄cycloalkyl, C₁-C₄alkylthio, C₁-C₃alkylsulfinyl,    C₁-C₃alkylsulfonyl, C₃-C₄cycloalkylsulfanyl,    C₃-C₄cycloalkylsulfinyl, C₃-C₄cycloalkylsulfonyl,    C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl; phenylsulfanyl    wherein the phenyl is optionally substituted with one to two    substituents selected from the group consisting of halogen, —CN,    C₁-C₃alkyl or C₁-C₃haloalkyl; phenylsulfinyl wherein the phenyl is    optionally substituted with one to two substituents selected from    the group consisting of halogen, —CN, C₁-C₃alkyl or C₁-C₃haloalkyl;    phenylsulfonyl wherein the phenyl is optionally substituted with one    to two substituents selected from the group consisting of halogen,    —CN, C₁-C₃alkyl or C₁-C₃haloalkyl; —NHCO-phenyl, wherein the phenyl    is optionally substituted with one to two substituents selected from    the group consisting of halogen, CN, C₁-C₆alkyl and C₁-C₃haloalkyl;    —CONH(C₃-C₄cycloalkyl), —CON(C₁-C₃alkyl)(C₃-C₄cycloalkyl),    —C(═NOC₁-C₃alkyl)-C₁-C₃alkyl; phenyl and 5- to 6-membered    heteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl is    optionally substituted with one to two substituents selected from    the group consisting of halogen, —CN, C₁-C₃alkyl, C₁-C₃haloalkyl and    C₁-C₃haloalkoxy;    -   the other one to two optional substituent(s) are each        independently selected from group B consisting of halogen, —CN,        —NO₂, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy,        C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl,        C₁-C₃alkylsulfonyl, C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl,        C₁-C₃haloalkylsulfonyl; phenyl and 5- to 6-membered heteroaryl,        wherein the phenyl and 5- to 6-membered heteroaryl is optionally        substituted with one to two substituents selected from the group        consisting of halogen, —CN, C₁-C₃alkyl and C₁-C₃haloalkyl;    -   or-   R² is thiophene, furane, pyrazole, thiazole, isothiazole, oxazole or    isoxazole each of which is optionally substituted by one to three    substituents independently selected from the group consisting of    halogen, hydroxy, —CN, —NO₂, C₁-C₆alkyl, C₃-C₄cycloalkyl,    C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio,    C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, C₃-C₄cycloalkylsulfanyl,    C₃-C₄cycloalkylsulfinyl, C₃-C₄cycloalkylsulfonyl,    C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl;    phenyl and 5- to 6-membered heteroaryl, wherein the phenyl or 5- to    6-membered heteroaryl is optionally substituted with one to two    substituents selected from the group consisting of halogen, —CN,    C₁-C₃alkyl and C₁-C₃haloalkyl    -   or-   R² is C₁-C₆alkyl substituted with one substituent selected from the    group consisting of C₁-C₃alkoxy-, C₁-C₃haloalkoxy-, C₁-C₃alkylthio,    C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, C₁-C₃haloalkylthio,    C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl; phenyl, wherein the    phenyl is optionally substituted with one to two substituents, each    independently selected from the group consisting of halogen, —CN,    C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy;-   R^(3a), R^(3b) are independently selected from the group consisting    of hydrogen; C₁-C₆alkyl optionally substituted by one to three    substituents independently selected from the group consisting of    C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy,    C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl,    C₁-C₃alkylsulfonyl, C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, and    C₁-C₃haloalkylsulfonyl; C₃-C₆cycloalkyl; C₁-C₆haloalkyl;    C₂-C₆alkenyl; C₂-C₆haloalkenyl; C₂-C₆alkynyl; C₂-C₆haloalkynyl;    benzyl wherein the phenyl substituent is optionally substituted with    one to three substituents independently selected from the group    consisting of halogen, —CN, —NO₂, C₁-C₆alkyl, C₁-C₃haloalkyl,    C₁-C₄alkoxy, and C₁-C₄haloalkoxy; or heterocyclyl-C₁-C₆alkyl wherein    the heterocyclyl substituent is selected from the group consisting    of 4- to 10-membered heterocyclyl, 5-membered heteroaryl and    6-membered heteroaryl, each of which is optionally substituted by    one to three substituents independently selected from the group    consisting of halogen, —CN, —NO₂, C₁-C₆alkyl, C₁-C₃haloalkyl, and    C₁-C₄alkoxy; or phenyl optionally substituted with one substituent    selected from the group consisting of halogen, —CN, —NO₂,    C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy;    -   or-   R^(3a), R^(3b) form together with the carbon to which they are    connected a cyclopropane, cyclobutane, oxetane or tetrahydropyrane    ring optionally substituted with one to two substituents, each    independently selected from the group consisting of halogen, —CN,    C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy;-   R⁴ is pyridine, pyrimidine or thiazole, wherein (A) the pyridine or    pyrimidine is optionally substituted with one to three substituents    selected from the group consisting of halogen, —CN, —NO₂,    C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy,    C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl,    C₁-C₃alkylsulfonyl, C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl and    C₁-C₃haloalkylsulfonyl and (B) the thiazole is optionally    substituted with one to two substituents selected from the group    consisting of halogen, —CN, —NO₂, C₁-C₆alkyl, C₃-C₆cycloalkyl,    C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio,    C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, C₁-C₃haloalkylthio,    C₁-C₃haloalkylsulfinyl and C₁-C₃haloalkylsulfonyl;-   R⁵ is hydrogen, halogen, —CN, C₁-C₃alkyl, C₁-C₃haloalkyl,    C₃-C₄cycloalkyl, or C₁-C₃alkoxy.

Also further preferred (Configuration 3-2) are the compounds of theformula (I) in which

-   X is O or S;-   Q¹ and Q² are independently CR⁵ or N, provided at least one of Q¹    and Q² is N; Y is a direct bond or CH₂;-   R¹ is hydrogen; C₁-C₃alkyl optionally substituted with one    substituent selected from —CN, —CONH₂, —COOH, —NO₂ and —Si(CH₃)₃;    C₁-C₃haloalkyl; C₂-C₄alkenyl; C₂-C₄haloalkenyl; C₁-C₄alkynyl;    C₁-C₄haloalkynyl; C₃-C₄cycloalkyl-C₁-C₂alkyl- wherein the    C₃-C₄cycloalkyl is optionally substituted with one or two halogen    atoms; oxetan-3-yl-CH₂—; or benzyl optionally substituted with    halogen or C₁-C₃haloalkyl;-   R² is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein    the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is    substituted with one to five substituents, provided at least one    substituent is on either carbon adjacent to the carbon bonded to the    C═X group, each independently selected from the group consisting of    -   halogen, —CN, —NO₂, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₃haloalkyl,        C₁-C₄alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio,        C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, C₃-C₄cycloalkylsulfanyl,        C₃-C₄cycloalkylsulfinyl, C₃-C₄cycloalkylsulfonyl,        C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl,        C₁-C₃haloalkylsulfonyl;    -   and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl        or 5- to 6-membered heteroaryl is optionally substituted with        one to two substituents selected from the group consisting of        halogen, —CN, C₁-C₃alkyl and C₁-C₃haloalkyl;    -   or-   R² is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein    the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is    substituted with a total of one to three substituents, provided the    substituent(s) are not on either carbon adjacent to the carbon    bonded to the C═X group and at least one and up to two    substituent(s) are independently selected from group A consisting of    -   C₄-alkyl, C₃-C₄cycloalkyl, wherein the C₃-C₄cycloalkyl is        optionally substituted with —CN or halogen, C₁-C₄alkylthio,        C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, C₃-C₄cycloalkylsulfanyl,        C₃-C₄cycloalkylsulfinyl, C₃-C₄cycloalkylsulfonyl,        C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl;    -   and phenylsulfanyl wherein the phenyl is optionally substituted        with one to two substituents selected from the group consisting        of halogen, —CN, C₁-C₃alkyl and C₁-C₃haloalkyl;    -   phenylsulfinyl wherein the phenyl is optionally substituted with        one to two substituents selected from the group consisting of        halogen, —CN, C₁-C₃alkyl and C₁-C₃haloalkyl;    -   phenylsulfonyl wherein the phenyl is optionally substituted with        one to two substituents selected from the group consisting of        halogen, —CN, C₁-C₃alkyl and C₁-C₃haloalkyl;    -   —NHCO-phenyl, wherein the phenyl is optionally substituted with        one to two substituents selected from the group consisting of        halogen, CN, C₁-C₆alkyl and C₁-C₃haloalkyl;    -   —NHCO—C₁-C₃alkyl, —NHCO—C₃-C₄cycloalkyl, —NHSO₂-phenyl;    -   —CONH(C₃-C₄cycloalkyl), —CON(C₁-C₃alkyl)(C₃-C₄cycloalkyl),        —C(═NOC₁-C₃alkyl)-C₁-C₃alkyl;    -   and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl        or 5- to 6-membered heteroaryl is optionally substituted with        one to two substituents selected from the group consisting of        halogen, —CN, C₁-C₃alkyl, C₁-C₃haloalkyl and C₁-C₃haloalkoxy;    -   and the other one to two optional substituent(s) are each        independently selected from group B consisting of    -   halogen, —CN, —NO₂, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₃haloalkyl,        C₁-C₄alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio,        C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, C₁-C₃haloalkylthio,        C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl;    -   and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl        and 5- to 6-membered heteroaryl is optionally substituted with        one to two substituents selected from the group consisting of        halogen, —CN, C₁-C₃alkyl and C₁-C₃haloalkyl;    -   or-   R² is thiophene, furane, pyrazole, thiazole, isothiazole, oxazole or    isoxazole each of which is optionally substituted by one to three    substituents independently selected from the group consisting of    -   halogen, hydroxy, —CN, —NO₂, C₁-C₆alkyl, C₃-C₄cycloalkyl,        C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio,        C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, C₃-C₄cycloalkylsulfanyl,        C₃-C₄cycloalkylsulfinyl, C₃-C₄cycloalkylsulfonyl,        C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl,        C₁-C₃haloalkylsulfonyl;    -   and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl        or 5- to 6-membered heteroaryl is optionally substituted with        one to two substituents selected from the group consisting of        halogen, —CN, C₁-C₃alkyl and C₁-C₃haloalkyl    -   or-   R² is C₁-C₆alkyl substituted with one substituent selected from the    group consisting of C₁-C₃alkoxy-, C₁-C₃haloalkoxy-, C₁-C₃alkylthio,    C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, C₁-C₃haloalkylthio,    C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl;    -   and phenyl, wherein the phenyl is optionally substituted with        one to two substituents, each independently selected from the        group consisting of halogen, —CN, C₁-C₆alkyl, C₁-C₃haloalkyl and        C₁-C₄alkoxy;    -   or-   R² is naphthyl optionally substituted by one to three substituents    independently selected from the group consisting of    -   halogen, hydroxy, —CN, —NO₂, C₁-C₆alkyl, C₃-C₄cycloalkyl,        C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio,        C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, C₃-C₄cycloalkylsulfanyl,        C₃-C₄cycloalkylsulfinyl, C₃-C₄cycloalkylsulfonyl,        C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl,        C₁-C₃haloalkylsulfonyl;    -   and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl        or 5- to 6-membered heteroaryl is optionally substituted with        one to two substituents selected from the group consisting of        halogen, —CN, C₁-C₃alkyl and C₁-C₃haloalkyl    -   or-   R² is a 9-membered or 10-membered heteroaryl, which is optionally    substituted by one to three substituents independently selected from    the group consisting of    -   halogen, hydroxy, —CN, —NO₂, C₁-C₆alkyl, C₃-C₄cycloalkyl,        C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio,        C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, C₃-C₄cycloalkylsulfanyl,        C₃-C₄cycloalkylsulfinyl, C₃-C₄cycloalkylsulfonyl,        C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl,        C₁-C₃haloalkylsulfonyl;    -   and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl        or 5- to 6-membered heteroaryl is optionally substituted with        one to two substituents selected from the group consisting of        halogen, —CN, C₁-C₃alkyl and C₁-C₃haloalkyl;-   R^(3a), R^(3b) are independently selected from the group consisting    of hydrogen; C₁-C₆alkyl optionally substituted by one to three    substituents independently selected from the group consisting of    C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy,    C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl,    C₁-C₃alkylsulfonyl, C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, and    C₁-C₃haloalkylsulfonyl; C₃-C₆cycloalkyl; C₁-C₆haloalkyl;    C₂-C₆alkenyl; C₁-C₆haloalkenyl; C₁-C₆alkynyl; C₁-C₆haloalkynyl;    benzyl wherein the phenyl substituent is optionally substituted with    one to three substituents independently selected from the group    consisting of halogen, —CN, —NO₂, C₁-C₆alkyl, C₁-C₃haloalkyl,    C₁-C₄alkoxy, and C₁-C₄haloalkoxy; or heterocyclyl-C₁-C₆alkyl wherein    the heterocyclyl substituent is selected from the group consisting    of 4- to 10-membered heterocyclyl, 5-membered heteroaryl and    6-membered heteroaryl, each of which is optionally substituted by    one to three substituents independently selected from the group    consisting of halogen, —CN, —NO₂, C₁-C₆alkyl, C₁-C₃haloalkyl, and    C₁-C₄alkoxy; or phenyl optionally substituted with one substituent    selected from the group consisting of halogen, —CN, —NO₂,    C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy;    -   or-   R^(3a), R^(3b) form together with the carbon to which they are    connected a cyclopropane, cyclobutane, oxetane or tetrahydropyrane    ring optionally substituted with one to two substituents, each    independently selected from the group consisting of halogen, —CN,    C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy;-   R⁴ is pyridine, pyrimidine, pyrazine, pyridazine or thiazole,    wherein (A) the pyridine, pyrimidine, pyrazine or pyridazine is    optionally substituted with one to three substituents selected from    the group consisting of halogen, —CN, —NH₂, —NO₂, —COOH, —CONH₂,    —CSNH₂, —CO₂—C₁-C₃alkyl, C₁-C₆alkyl, C₃-C₆cycloalkyl,    C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio,    C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, C₁-C₃haloalkylthio,    C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl, —NHCO—C₁-C₃alkyl,    —NHCO—C₁-C₃haloalkyl, —NHCO—C₁-C₃cyanoalkyl, —NHCO—C₃-C₄cycloalkyl,    wherein the cycloalkyl is optionally substituted with one to two    substituents selected from the group consisting of fluorine,    chlorine, —CN, C₁-C₆alkyl or C₁-C₄alkoxy; —NHCO-phenyl, wherein the    phenyl is optionally substituted with one to two substituents    selected from the group consisting of halogen, —CN, C₁-C₃alkyl,    C₁-C₃haloalkyl, C₁-C₃alkoxy and C₁-C₃haloalkoxy; —NHSO₂—C₁-C₃alkyl,    —NHSO₂—C₁-C₃haloalkyl, —CONH(C₁-C₃alkyl), —CON(C₁-C₃alkyl)₂,    —CONH—SO₂—C₁-C₃alkyl, —CON(C₁-C₃alkyl)(C₃-C₆cycloalkyl),    —CONH(C₁-C₃haloalkyl), —CONH(C₃-C₆cycloalkyl),    —CONH(1-cyano-C₃-C₆cycloalkyl), —CONH-phenyl, wherein the phenyl is    optionally substituted with one to two substituents selected from    the group consisting of halogen, —CN, C₁-C₃alkyl, C₁-C₃haloalkyl,    C₁-C₃alkoxy and C₁-C₃haloalkoxy;    -   and (B) the thiazole is optionally substituted with one to two        substituents selected from the group consisting of halogen, —CN,        —NO₂, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy,        C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl,        C₁-C₃alkylsulfonyl, C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl        and C₁-C₃haloalkylsulfonyl;-   R⁵ is hydrogen, halogen, —CN, C₁-C₃alkyl, C₁-C₃haloalkyl,    C₃-C₄cycloalkyl, or C₁-C₃alkoxy.

Particularly preferred (Configuration 4-1) are the compounds of theformula (I) in which

-   X is O or S;-   Q¹ and Q² are independently CR⁵ or N, provided at least one of Q¹    and Q² is N;-   Y is a direct bond or CH₂;-   R¹ is hydrogen; C₁-C₃alkyl optionally substituted with —CN,    —Si(CH₃)₃ or one to three substituents selected from the group    consisting of fluorine, chlorine or bromine; C₂-C₄alkenyl;    C₂-C₄alkynyl; C₃-C₄cycloalkyl-C₁-C₂alkyl- wherein the    C₃-C₄cycloalkyl is optionally substituted with one to two    substituents selected from the group consisting of fluorine,    chlorine and bromine;-   R² is phenyl or pyridine wherein the phenyl or pyridine is    substituted with one to three substituents, provided at least one    substituent is on either carbon adjacent to the carbon bonded to the    C═X group, each independently selected from the group consisting of    fluorine, chlorine, bromine, —CN, —NO₂, methyl, cyclopropyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy,    difluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl,    ethylthio, ethylsulfinyl, ethylsulfonyl, isopropylthio,    isopropylsulfinyl, isopropylsulfonyl, cyclopropylthio,    cyclopropylsulfinyl, cyclopropylsulfonyl, difluoromethylthio,    difluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylthio,    trifluoromethylsulfinyl, trifluoromethylsulfonyl, and phenyl,    wherein the phenyl is optionally substituted with one two    substituents selected from the group consisting of fluorine,    chlorine, bromine, —CN, difluoromethyl and trifluoromethyl;    -   or-   R² is phenyl or pyridine, wherein the phenyl or pyridine is    substituted with a total of one to three substituents, provided the    substituent(s) are not on either carbon adjacent to the carbon    bonded to the C═X group and one substituent is independently    selected from group A consisting of cyclopropyl, methylthio,    methylsulfinyl, methylsulfonyl, ethylthio, ethylsulfinyl,    ethylsulfonyl, isopropylthio, isopropylsulfinyl, isopropylsulfonyl,    tert-butylthio, tert-butylsulfinyl, tert-butylsulfonyl,    cyclopropylthio, cyclopropylsulfinyl, cyclopropylsulfonyl,    difluoromethylsulfinyl, difluoromethylsulfonyl,    trifluoromethylsulfinyl, trifluoromethylsulfonyl; phenylsulfonyl    wherein the phenyl is optionally substituted with one two    substituents selected from the group consisting of fluorine,    chlorine bromine, —CN, difluoromethyl and trifluoromethyl;    —NHCO-phenyl wherein the phenyl is optionally substituted with one    to two substituents selected from the group consisting of fluorine,    chlorine, CN, methyl and trifluoromethyl;    (cyclopropylamino)carbonyl, 1-(methoxyimino)ethyl; phenyl and    5-membered heteroaryl wherein the phenyl or 5-membered heteroaryl is    optionally substituted with one two substituents selected from the    group consisting of fluorine, chlorine bromine, —CN, difluoromethyl,    trifluoromethyl and trifluoromethoxy;    -   the other one to two optional substituent(s) are each        independently selected from group B consisting of fluorine,        chlorine, bromine, —CN, —NO₂, methyl, cyclopropyl,        difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy,        difluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl,        difluoromethylthio, difluoromethylsulfinyl,        difluoromethylsulfonyl, trifluoromethylthio,        trifluoromethylsulfinyl, trifluoromethylsulfonyl and phenyl,        wherein the phenyl is optionally substituted with one two        substituents selected from the group consisting of fluorine,        chlorine bromine, —CN, difluoromethyl and trifluoromethyl;    -   or-   R² is thiophene, furane, pyrazole, thiazole, oxazole or isoxazole    each of which is optionally substituted by one to three substituents    independently selected from the group consisting of of fluorine,    chlorine, bromine, —CN, —NO₂, methyl, cyclopropyl, difluoromethyl,    trifluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy,    methylthio, methylsulfinyl, methylsulfonyl, difluoromethylthio,    difluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylthio,    trifluoromethylsulfinyl, trifluoromethylsulfonyl and phenyl, wherein    the phenyl is optionally substituted with one two substituents    selected from the group consisting of fluorine, chlorine, bromine,    —CN, difluoromethyl and trifluoromethyl    -   or-   R² is C₁-C₃alkyl substituted with one substituent selected from the    group consisting of methoxy, trifluoromethoxy, difluoromethoxy,    methylthio, methylsulfinyl, methylsulfonyl, difluoromethylthio,    difluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylthio,    trifluoromethylsulfinyl, trifluoromethylsulfonyl and phenyl, wherein    the phenyl is optionally substituted with one two substituents    selected from the group consisting of fluorine, chlorine, bromine,    —CN, difluoromethyl and trifluoromethyl;-   R^(3a), R^(3b) are independently selected from the group consisting    of hydrogen; C₁-C₃alkyl optionally substituted by one to three    substituents independently selected from the group consisting of    methyl, ethyl, iso-propyl, n-propyl, cyclopropyl, cyclobutyl,    difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy,    trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl,    trifluoromethylthio, trifluoromethylsulfinyl, and    trifluoromethylsulfonyl; cyclopropyl, difluoromethyl,    trifluoromethyl, difluoromethyl, trifluoromethyl, 2,2-difluoroethyl,    2,2,2-trifluoroethyl, ethinyl, 2-propen-1-yl and 2-propin-1-yl;    benzyl wherein the phenyl substituent is optionally substituted with    one to three substituents independently selected from the group    consisting of fluorine, chlorine, bromine, —CN, NO₂, methyl,    trifluoromethyl and methoxy; heterocyclyl-methyl wherein the    heterocyclyl substituent is selected from the group consisting of 4-    to 10-membered heterocyclyl, 5-membered heteroaryl and 6-membered    heteroaryl, each of which is optionally substituted by one to three    substituents independently selected from the group consisting of    fluorine, chlorine, bromine, —CN, —NO₂, methyl, trifluoromethyl and    methoxy; and phenyl optionally substituted with one substituent    selected from the group consisting of fluorine, chlorine, bromine,    —CN, —NO₂, methyl, trifluoromethyl and methoxy;    -   or-   R^(3a), R^(3b) form together with the carbon to which they are    connected a cyclopropane, cyclobutane, oxetane or tetrahydropyrane    ring;-   R⁴ is pyridine, pyrimidine or thiazole, wherein (A) the pyridine or    pyrimidine is optionally substituted with one to three substituents    selected from the group consisting of fluorine, chlorine, bromine,    —CN, —NO₂, methyl, ethyl, difluoromethyl, trifluoromethyl,    pentafluoroethyl, cyclopropyl, methoxy, difluoromethoxy,    trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl,    difluoromethylthio, difluoromethylsulfinyl, difluoromethylsulfonyl,    trifluoromethylthio, trifluoromethylsulfinyl and    trifluoromethylsulfonyl and (B) the thiazole is optionally    substituted with one to two substituents selected from the group    consisting of fluorine, chlorine, bromine, —CN, —NO₂, methyl, ethyl,    difluoromethyl, trifluoromethyl, pentafluoroethyl, cyclopropyl,    methoxy, difluoromethoxy, trifluoromethoxy, methylthio,    methylsulfinyl, methylsulfonyl, difluoromethylthio,    difluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylthio,    trifluoromethylsulfinyl and trifluoromethylsulfonyl;-   R⁵ is hydrogen, fluorine, chlorine, bromine, —CN, methyl, ethyl,    iso-propyl, difluoromethyl, trifluoromethyl, cyclopropyl, methoxy,    or ethoxy.

Particular preference is also given (Configuration 4-2) to the compoundsof the formula (I) in which

-   X is O or S;-   Q¹ and Q² are independently CR⁵ or N, provided at least one of Q¹    and Q² is N;-   Y is a direct bond or CH₂;-   R¹ is hydrogen; C₁-C₃alkyl optionally substituted with —CN,    —Si(CH₃)₃ or one to three substituents selected from the group    consisting of fluorine, chlorine or bromine; C₂-C₄alkenyl;    C₂-C₄alkynyl; C₃-C₄cycloalkyl-C₁-C₂alkyl- wherein the    C₃-C₄cycloalkyl is optionally substituted with one to two    substituents selected from the group consisting of fluorine,    chlorine and bromine;-   R² is phenyl or pyridine wherein the phenyl or pyridine is    substituted with one to three substituents, provided at least one    substituent is on either carbon adjacent to the carbon bonded to the    C═X group, each independently selected from the group consisting of    -   fluorine, chlorine, bromine, —CN, —NO₂, methyl, cyclopropyl,        difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy,        difluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl,        ethylthio, ethylsulfinyl, ethylsulfonyl, isopropylthio,        isopropylsulfinyl, isopropylsulfonyl, cyclopropylthio,        cyclopropylsulfinyl, cyclopropylsulfonyl, difluoromethylthio,        difluoromethylsulfinyl, difluoromethylsulfonyl,        trifluoromethylthio, trifluoromethylsulfinyl,        trifluoromethylsulfonyl,    -   and phenyl, wherein the phenyl is optionally substituted with        one two substituents selected from the group consisting of        fluorine, chlorine, bromine, —CN, difluoromethyl and        trifluoromethyl;    -   or-   R² is phenyl or pyridine, wherein the phenyl or pyridine is    substituted with a total of one to three substituents, provided the    substituent(s) are not on either carbon adjacent to the carbon    bonded to the C═X group and one substituent is independently    selected from group A consisting of    -   tert-butyl, cyclopropyl, 1-cyanocyclopropyl, methylthio,        methylsulfinyl, methylsulfonyl, ethylthio, ethylsulfinyl,        ethylsulfonyl, isopropylthio, isopropylsulfinyl,        isopropylsulfonyl, tert-butylthio, tert-butylsulfinyl,        tert-butylsulfonyl, cyclopropylthio, cyclopropylsulfinyl,        cyclopropylsulfonyl, difluoromethylsulfinyl,        difluoromethylsulfonyl, trifluoromethylsulfinyl,        trifluoromethylsulfonyl, trifluoroethylsulfinyl,        trifluoroethylsulfonyl;    -   phenylsulfonyl wherein the phenyl is optionally substituted with        one two substituents selected from the group consisting of        fluorine, chlorine, bromine, —CN, difluoromethyl and        trifluoromethyl;    -   —NHCO-phenyl wherein the phenyl is optionally substituted with        one to two substituents selected from the group consisting of        fluorine, chlorine, CN, methyl and trifluoromethyl;    -   (cyclopropylamino)carbonyl, 1-(methoxyimino)ethyl, acetamido,        (cyclopropylcarbonyl)amino, (phenylsulfonyl)amino;    -   and phenyl and 5-membered heteroaryl wherein the phenyl or        5-membered heteroaryl is optionally substituted with one two        substituents selected from the group consisting of fluorine,        chlorine bromine, —CN, difluoromethyl, trifluoromethyl and        trifluoromethoxy;    -   and the other one to two optional substituent(s) are each        independently selected from group B consisting of    -   fluorine, chlorine, bromine, —CN, —NO₂, methyl, cyclopropyl,        difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy,        difluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl,        difluoromethylthio, difluoromethylsulfinyl,        difluoromethylsulfonyl, trifluoromethylthio,        trifluoromethylsulfinyl, trifluoromethylsulfonyl    -   and phenyl, wherein the phenyl is optionally substituted with        one two substituents selected from the group consisting of        fluorine, chlorine bromine, —CN, difluoromethyl and        trifluoromethyl;    -   or-   R² is thiophene, furane, pyrazole, thiazole, oxazole or isoxazole    each of which is optionally substituted by one to three substituents    independently selected from the group consisting of of    -   fluorine, chlorine, bromine, —CN, —NO₂, methyl, cyclopropyl,        difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy,        difluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl,        difluoromethylthio, difluoromethylsulfinyl,        difluoromethylsulfonyl, trifluoromethylthio,        trifluoromethylsulfinyl, trifluoromethylsulfonyl    -   and phenyl, wherein the phenyl is optionally substituted with        one two substituents selected from the group consisting of        fluorine, chlorine, bromine, —CN, difluoromethyl and        trifluoromethyl    -   or-   R² is C₁-C₃alkyl substituted with one substituent selected from the    group consisting of    -   methoxy, trifluoromethoxy, difluoromethoxy, methylthio,        methylsulfinyl, methylsulfonyl, difluoromethylthio,        difluoromethylsulfinyl, difluoromethylsulfonyl,        trifluoromethylthio, trifluoromethylsulfinyl,        trifluoromethylsulfonyl    -   and phenyl, wherein the phenyl is optionally substituted with        one two substituents selected from the group consisting of        fluorine, chlorine, bromine, —CN, difluoromethyl and        trifluoromethyl    -   or-   R² is naphthyl; or pyrazolo[1.5-a]pyridin-2-yl, optionally    substituted with trifluoromethyl or chlorine;-   R^(3a), R^(3b) are independently selected from the group consisting    of hydrogen; C₁-C₃alkyl optionally substituted by one to three    substituents independently selected from the group consisting of    methyl, ethyl, iso-propyl, n-propyl, cyclopropyl, cyclobutyl,    difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy,    trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl,    trifluoromethylthio, trifluoromethylsulfinyl, and    trifluoromethylsulfonyl; cyclopropyl, difluoromethyl,    trifluoromethyl, difluoromethyl, trifluoromethyl, 2,2-difluoroethyl,    2,2,2-trifluoroethyl, ethinyl, 2-propen-1-yl and 2-propin-1-yl;    benzyl wherein the phenyl substituent is optionally substituted with    one to three substituents independently selected from the group    consisting of fluorine, chlorine, bromine, —CN, NO₂, methyl,    trifluoromethyl and methoxy; heterocyclyl-methyl wherein the    heterocyclyl substituent is selected from the group consisting of 4-    to 10-membered heterocyclyl, 5-membered heteroaryl and 6-membered    heteroaryl, each of which is optionally substituted by one to three    substituents independently selected from the group consisting of    fluorine, chlorine, bromine, —CN, —NO₂, methyl, trifluoromethyl and    methoxy; and phenyl optionally substituted with one substituent    selected from the group consisting of fluorine, chlorine, bromine,    —CN, —NO₂, methyl, trifluoromethyl and methoxy;    -   or-   R^(3a), R^(3b) form together with the carbon to which they are    connected a cyclopropane, cyclobutane, oxetane or tetrahydropyrane    ring;-   R⁴ is pyridine, pyrimidine, pyrazine or thiazole, wherein (A) the    pyridine, pyrimidine or pyrazine is optionally substituted with one    to three substituents selected from the group consisting of    fluorine, chlorine, bromine, —CN, —NH₂, —NO₂, —COOH, —CONH₂, —CSNH₂,    —CO₂Me, methyl, ethyl, difluoromethyl, trifluoromethyl,    pentafluoroethyl, cyclopropyl, methoxy, difluoromethoxy,    trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl,    difluoromethylthio, difluoromethylsulfinyl, difluoromethylsulfonyl,    trifluoromethylthio, trifluoromethylsulfinyl,    trifluoromethylsulfonyl, —NHCO-methyl, —NHCO-trifluoromethyl,    —NHCO—CH₂CN, —NHCO-cyclopropyl, —NHCO-1-cyanocyclopropyl,    —NHSO₂-methyl, —NHSO₂-trifluoromethyl, —NHCO-phenyl, wherein the    phenyl is optionally substituted with one to two substituents    selected from the group consisting of fluorine, chlorine, bromine,    —CN, methyl, difluoromethyl, trifluoromethyl, methoxy,    difluoromethoxy and trifluoromethoxy; —CONH-methyl,    —CONH—SO₂-methyl, —CON—(N-methyl)-N-cyclopropyl,    —CONH-difluoroethyl, —CONH-trifluoroethyl, —CONH-cyclopropyl,    —CONH-1-cyanocyclopropyl, —CONH-phenyl, wherein the phenyl is    optionally substituted with one to two substituents selected from    the group consisting of fluorine, chlorine, bromine, —CN, methyl,    difluoromethyl, trifluoromethyl, methoxy, difluoromethoxy and    trifluoromethoxy;    -   and (B) the thiazole is optionally substituted with one to two        substituents selected from the group consisting of fluorine,        chlorine, bromine, —CN, —NO₂, methyl, ethyl, difluoromethyl,        trifluoromethyl, pentafluoroethyl, cyclopropyl, methoxy,        difluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl,        methylsulfonyl, difluoromethylthio, difluoromethylsulfinyl,        difluoromethylsulfonyl, trifluoromethylthio,        trifluoromethylsulfinyl and trifluoromethylsulfonyl;-   R⁵ is hydrogen, fluorine, chlorine, bromine, —CN, methyl, ethyl,    iso-propyl, difluoromethyl, trifluoromethyl, cyclopropyl, methoxy,    or ethoxy.

Very particularly preferred (Configuration 5-1) are the compounds of theformula (I) in which

-   X is O;-   Q¹ is N-   Q² is CR⁵-   Y is a direct bond;-   R¹ is hydrogen, cyclopropyl-CH₂—, 3,3,3-trifluoropropyl, ethyl or    2,2-difluoroethyl;-   R² 3-chloro-2-fluoro-5-(trifluoromethyl)phenyl,    3-chloro-5-(methylsulfonyl)phenyl, 5-(methylsulfonyl)pyridin-3-yl,    3-(methylsulfonyl)phenyl, 3-(trifluoromethylsulfonyl)phenyl,    5-[(trifluoromethyl)sulfonyl]pyridin-3-yl,    3-chloro-5-[(cyclopropylamino)carbonyl]phenyl,    3-cyclopropyl-5-(trifluoromethyl)phenyl, 2,3,5-trichlorophenyl,    3-phenyl-5-(trifluoromethyl)phenyl,    [3-chloro-5-(trifluoromethyl)phenyl]methyl,    3-(4-fluorophenyl)-5-(trifluoromethyl)phenyl, 2-chlorophenyl,    2,5-dichlorophenyl, 2,3,4-trichlorophenyl, 2,3-dichlorophenyl,    2,4-dichlorophenyl, 2,6-difluorophenyl,    3-chloro-5-(trifluoromethylsulfonyl)phenyl, 5-chloro-3-thienyl,    3,4,5-trichloro-2-thienyl, 2,5-dichloro-3-thienyl,    4,5-dichloro-2-thienyl,    1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl,    4-chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl,    5-methyl-1,2-oxazol-3-yl, 5-cyclopropyl-1,2-oxazol-3-yl,    3-chloro-1,2-oxazol-5-yl, 2-chloro-1,3-thiazol-5-yl,    1-methyl-H-pyrazol-4-yl, 5-chloro-1-methyl-1H-pyrazol-4-yl,    3-chloro-5-cyclopropylsulfonylphenyl,    3-chloro-5-(4-fluorophenyl)sulfonylphenyl,    3-chloro-5-ethylsulfonylphenyl, 3-cyclopropyl-5-fluorophenyl,    3-chloro-5-(isopropylthio)phenyl,    3-chloro-5-(1H-pyrazol-1-yl)phenyl,    3-chloro-5-(1H-1,2,4-triazol-1-yl)phenyl,    3-chloro-5-cyclopropylphenyl, 3-chloro-5-isopropylsulfonylphenyl,    1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl,    3-cyclopropyl-5-(trifluoromethoxy)phenyl,    4-(trifluoromethylsulfonyl)phenyl,    3-chloro-5-[1-(methoxyimino)ethyl]phenyl,    3-(tert-butylthio)-5-chlorophenyl,    1-(4-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-3-yl,    5-[4-(trifluoromethoxy)phenyl]pyridin-3-yl,    3-chloro-5-methylsulfanylphenyl, 3-chloro-5-methylsulfinylphenyl, or    3-benzamido-5-chlorophenyl;-   R^(3a) is hydrogen, methyl or methoxymethyl;-   R^(3b) is methyl or methoxymethyl if R^(3a) is hydrogen;-   R^(3b) is hydrogen if R^(3a) is methyl or methoxymethyl;-   R⁴ is 2-pyridinyl, 2-pyrimidin-2-yl, 2-pyrimidin-4-yl,    5-chloropyridin-2-yl, 4-chloropyridin-2-yl, 5-cyanopyridin-2-yl,    4-cyano-2-pyridinyl, 5-(trifluoromethyl)-pyridin-2-yl,    5-(difluoromethoxy)pyridin-2-yl,    5-(trifluoromethylthio)pyridin-2-yl, 3,5-difluoro-2-pyridinyl,    5-chloro-3-fluoro-2-pyridinyl, 5-fluoropyrimidin-2-yl,    5-chloropyrimidin-2-yl, 2-pyrazin-2-yl or 1,3-thiazol-2-yl;-   R⁵ is hydrogen or methyl.

Very particular preference is also given (Configuration 5-2) to thecompounds of the formula (I) in which

-   X is O or S;-   Q¹ is N-   Q² is CR⁵-   Y is a direct bond or CH₂;-   R¹ is hydrogen, methyl, ethyl, 2-(trimethylsilyl)ethyl,    2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, or    cyclopropyl-CH₂—;-   R² 3-chloro-2-fluoro-5-(trifluoromethyl)phenyl,    3-chloro-5-(methylsulfonyl)phenyl,    3-methylsulfonyl-5-(trifluoromethyl)phenyl,    5-(methylsulfonyl)pyridin-3-yl, 3-(methylsulfonyl)phenyl,    3-(trifluoromethylsulfonyl)phenyl,    5-[(trifluoromethyl)sulfonyl]pyridin-3-yl,    3-chloro-5-[(cyclopropylamino)carbonyl]phenyl,    3-cyclopropyl-5-(trifluoromethyl)phenyl, 2,3,5-trichlorophenyl,    3-phenyl-5-(trifluoromethyl)phenyl,    [3-chloro-5-(trifluoromethyl)phenyl]methyl,    3-(4-fluorophenyl)-5-(trifluoromethyl)phenyl, 2-chlorophenyl,    2,5-dichlorophenyl, 2,3,4-trichlorophenyl, 2,3-dichlorophenyl,    2,4-dichlorophenyl, 2,6-difluorophenyl,    3-fluoro-5-(trifluoromethylsulfonyl)phenyl,    3-chloro-5-(trifluoromethylsulfonyl)phenyl, 5-chloro-3-thienyl,    3,4,5-trichloro-2-thienyl, 2,5-dichloro-3-thienyl,    4,5-dichloro-2-thienyl,    1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl,    4-chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl,    5-methyl-1,2-oxazol-3-yl, 5-cyclopropyl-1,2-oxazol-3-yl,    3-chloro-1,2-oxazol-5-yl, 2-chloro-1,3-thiazol-5-yl,    1-methyl-1H-pyrazol-4-yl, 5-chloro-1-methyl-1H-pyrazol-4-yl,    3-chloro-5-cyclopropylsulfonylphenyl,    3-chloro-5-(4-fluorophenyl)sulfonylphenyl,    3-chloro-5-ethylsulfonylphenyl, 3-cyclopropyl-5-fluorophenyl,    3-chloro-5-(isopropylthio)phenyl,    3-chloro-5-(1H-pyrazol-1-yl)phenyl,    3-chloro-5-(1H-1,2,4-triazol-1-yl)phenyl,    3-tert-butyl-5-chlorophenyl, 3-tert-butyl-5-bromophenyl,    3-fluoro-5-cyclopropylphenyl, 3-chloro-5-cyclopropylphenyl,    3-chloro-5-isopropylsulfonylphenyl,    1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl,    3-cyclopropyl-5-(trifluoromethoxy)phenyl,    4-(trifluoromethylsulfonyl)phenyl,    3-chloro-5-[1-(methoxyimino)ethyl]phenyl,    3-(tert-butylthio)-5-chlorophenyl,    1-(4-fluorophenyl)-1H-pyrazol-4-yl,    1-(4-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-3-yl,    5-[4-(trifluoromethoxy)phenyl]pyridin-3-yl,    3-chloro-5-methylsulfanylphenyl, 3-chloro-5-methylsulfinylphenyl,    3-benzamido-5-chlorophenyl, 3-(tert-butylsulfonyl)-5-chlorophenyl,    5-[4-(trifluoromethyl)phenyl]-pyridin-3-yl,    5-[4-(trifluoromethoxy)phenyl]-pyridin-3-yl,    5-(4-chlorophenyl)pyridin-3-yl, 5-(4-fluorophenyl)pyridin-3-yl,    3-chloro-5-[(phenylsulfonyl)amino]phenyl,    3-acetamido-5-chlorophenyl,    3-chloro-5-[(cyclopropylcarbonyl)amino]phenyl,    3-chloro-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl,    3-chloro-5-[(2,2,2-trifluoroethyl)sulfonyl]phenyl,    3-chloro-5-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl,    3,5-bis(methylsulfonyl)phenyl, pyrazolo[1,5-a]pyridin-2-yl,    7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl,    6-chloropyrazolo[1,5-a]pyridin-2-yl, naphth-2-yl,    3-[4′-(trifluoromethoxy)phenyl]-phenyl,    3-(4′-fluorophenyl)-5-(trifluoromethyl)phenyl or    3-chloro-5-(1-cyanocyclopropyl)phenyl;-   R^(3a) is hydrogen, methyl or methoxymethyl;-   R^(3b) is methyl or methoxymethyl if R^(3a) is hydrogen;-   R^(3b) is hydrogen if R^(3a) is methyl or methoxymethyl;-   R^(3a) and R^(3b) form together with the carbon to which they are    connected a cyclopropane ring;-   R⁴ is pyridin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl,    5-fluoropyrimidin-2-yl, 5-chloropyrimidin-2-yl,    5-cyanopyrimidin-2-yl, 5-(trifluoromethyl)pyrimidin-2-yl,    5-methylpyrimidin-2-yl, 5-fluoropyridin-2-yl, 5-chloropyridin-2-yl,    2-chloropyridin-4-yl, 5-cyanopyridin-2-yl, 4-cyano-pyridin-2-yl,    6-cyano-pyridin-2-yl, 5-methoxy-pyridin-2-yl,    5-(trifluoromethyl)-pyridin-2-yl, 5-(difluoromethoxy)pyridin-2-yl,    5-(trifluoromethylthio)pyridin-2-yl, 5-nitropyridin-2-yl,    5-aminopyridin-2-yl, 3,5-difluoropyridin-2-yl,    5-chloro-3-fluoropyridin-2-yl, pyridin-2-yl-5-carboxylic acid,    methyl pyridin-2-yl-5-carboxylate,    N-methyl-pyridin-2-yl-5-carboxamide,    N-cyclopropyl-pyridin-2-yl-5-carboxamide,    N-cyclopropyl-N-methyl-pyridin-2-yl-5-carboxamide,    N-(1-cyanocyclopropyl)-pyridin-2-yl-5-carboxamide,    N-(2,2-difluoroethyl)-pyridin-2-yl-5-carboxamide,    N-(2,2,2-trifluoroethyl)-pyridin-2-yl-5-carboxamide,    N-methylsulfonyl-pyridin-2-yl-5-carboxamide,    N-(4-fluorophenyl)-pyridin-2-yl-5-carboxamide,    5-acetamidopyridin-2-yl, 5-(trifluoroacetamido)-pyridin-2-yl,    5-(2-cyanoacetylamino)-pyridin-2-yl,    5-[(cyclopropylcarbonyl)amino]pyridin-2-yl,    5-[(1-cyanocyclopropylcarbonyl)amino]-pyridin-2-yl,    5-(methanesulfonamido)-pyridin-2-yl,    5-(trifluoromethylsulfonamido)-pyridin-2-yl,    5-[(4-fluorobenzoyl)amino]pyridine-2-yl pyrazin-2-yl,    2-cyano-pyrazin-5-yl, or 1,3-thiazol-2-yl;-   R⁵ is hydrogen, methyl or trifluoromethyl.

In a further preferred embodiment, the invention relates to compounds ofthe formula (I′)

in which the structural elements Y, Q¹, Q², R¹, R², R^(3a), R^(3b), R⁴and R⁵ have the meanings given in Configuration (1-1) or inConfiguration (2-1) or in Configuration (3-1) or in Configuration (4-1)or in Configuration (5-1).

In another further preferred embodiment, the invention relates tocompounds of the formula (I′)

in which the structural elements Y, Q¹, Q², R¹, R², R^(3a), R^(3b), R⁴and R⁵ have the meanings given in Configuration (1-2) or inConfiguration (2-2) or in Configuration (3-2) or in Configuration (4-2)or in Configuration (5-2).

In further preferred embodiments of the compounds of the formula (I′),Q¹ represents N or CR⁵ and Q² represents N and all further structuralelements Y, R¹, R², R^(3a), R^(3b), R⁴ and R⁵ have the meaningsdescribed above in Configuration (1-1) or in Configuration (2-1) or inConfiguration (3-1) or in Configuration(4-1) or in Configuration (5-1).

In another further preferred embodiments of the compounds of the formula(I′), Q¹ represents N or CR⁵ and Q² represents N and all furtherstructural elements Y, R¹, R², R^(3a), R^(3b), R⁴ and R⁵ have themeanings described above in Configuration (1-2) or in Configuration(2-2) or in Configuration (3-2) or in Configuration (4-2) or inConfiguration (5-2).

In other further preferred embodiments of the compounds of the formula(I′), Q¹ represents N and Q² represents CR and all further structuralelements Y, R¹, R², R^(3a), R^(3b), R⁴ and R⁵ have the meaningsdescribed above in Configuration (1-1) or in Configuration (2-1) or inConfiguration (3-1) or in Configuration (4-1) or in Configuration (5-1).

In another further preferred embodiments of the compounds of the formula(I′), Q¹ represents N and Q² represents CR⁵ and all further structuralelements Y, R¹, R², R^(3a), R^(3b), R⁴ and R⁵ have the meaningsdescribed above in Configuration (1-2) or in Configuration (2-2) or inConfiguration (3-2) or in Configuration (4-2) or in Configuration (5-2).

Among these, particular preference is given to the configurations shownbelow:

Compounds of the with with all other structural formula Q¹ as per Q² asper elements as per I′ N CR⁵ Configuration (1-1) I′ N CR⁵ Configuration(2-1) I′ N CR⁵ Configuration (3-1) I′ N CR⁵ Configuration (4-1) I′ N CR⁵Configuration (5-1) I′ CR⁵ N Configuration (1-1) I′ CR⁵ N Configuration(2-1) I′ CR⁵ N Configuration (3-1) I′ CR⁵ N Configuration (4-1) I′ CR⁵ NConfiguration (5-1) I′ N N Configuration (1-1) I′ N N Configuration(2-1) I′ N N Configuration (3-1) I′ N N Configuration (4-1) I′ N NConfiguration (5-1) I′ N CR⁵ Configuration (1-2) I′ N CR⁵ Configuration(2-2) I′ N CR⁵ Configuration (3-2) I′ N CR⁵ Configuration (4-2) I′ N CR⁵Configuration (5-2) I′ CR⁵ N Configuration (1-2) I′ CR⁵ N Configuration(2-2) I′ CR⁵ N Configuration (3-2) I′ CR⁵ N Configuration (4-2) I′ CR⁵ NConfiguration (5-2) I′ N N Configuration (1-2) I′ N N Configuration(2-2) I′ N N Configuration (3-2) I′ N N Configuration (4-2) I′ N NConfiguration (5-2)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I″) in which R^(3b) is C₁-C₃alkyl, especially preferred Me,and R^(3a) is H

in which the structural elements Y, Q¹, Q², R¹, R², R⁴ and R⁵ have themeanings given in Configuration (1-1) or in Configuration (2-1) or inConfiguration (3-1) or in Configuration (4-1) or in Configuration (5-1).

In another further preferred embodiment, the invention relates tocompounds of the formula (I″) in which R^(3b) is C₁-C₃alkyl, especiallypreferred Me, and R^(3a) is H

in which the structural elements Y, Q¹, Q², R¹, R², R⁴ and R⁵ have themeanings given in Configuration (1-2) or in Configuration (2-2) or inConfiguration (3-2) or in Configuration (4-2) or in Configuration (5-2).

In a further preferred embodiment, the invention relates to compounds ofthe formula (I′″) in which R^(3b) is C₁-C₃alkyl, especially preferredMe, and R^(3a) is H

in which the structural elements Y, Q¹, Q², R¹, R², R⁴ and R⁵ have themeanings given in Configuration (1-1) or in Configuration (2-1) or inConfiguration (3-1) or in Configuration (4-1) or in Configuration (5-1).

In another further preferred embodiment, the invention relates tocompounds of the formula (I′″) in which R^(3b) is C₁-C₃alkyl, especiallypreferred Me, and R^(3a) is H

in which the structural elements Y, Q¹, Q², R¹, R², R⁴ and R⁵ have themeanings given in Configuration (1-2) or in Configuration (2-2) or inConfiguration (3-2) or in Configuration (4-2) or in Configuration (5-2).

In a further preferred embodiment, the invention relates to compounds ofthe formula (I′p1)

in which Y is a direct bond and the structural elements R¹, R², R^(3a),R^(3b), R⁴ and R⁵ have the meanings given the following table:

R¹ R² R^(3a), R^(3b) R⁴ R⁵ meaning meaning meaning meaning meaning givenin given in given in given in given in Configu- Configu- Configu-Configu- Configu- entry ration ration ration ration ration 1 4-1 4-1 5-14-1 4-1 2 4-1 4-1 5-1 4-1 5-1 3 4-1 4-1 5-1 5-1 4-1 4 4-1 5-1 5-1 4-14-1 5 4-1 5-1 5-1 5-1 4-1 6 4-1 5-1 5-1 4-1 5-1 7 4-1 4-1 5-1 5-1 5-1 84-1 5-1 5-1 5-1 5-1 9 5-1 4-1 5-1 4-1 4-1 10 5-1 4-1 5-1 4-1 5-1 11 5-14-1 5-1 5-1 4-1 12 5-1 5-1 5-1 4-1 4-1 13 5-1 5-1 5-1 5-1 4-1 14 5-1 5-15-1 4-1 5-1 15 5-1 4-1 5-1 5-1 5-1 16 5-1 5-1 5-1 5-1 5-1 17 4-1 3-1 5-14-1 4-1 18 4-1 3-1 5-1 4-1 5-1 19 4-1 3-1 5-1 5-1 4-1 20 4-1 3-1 5-1 5-15-1 21 5-1 3-1 5-1 4-1 4-1 22 5-1 3-1 5-1 4-1 5-1 23 5-1 3-1 5-1 5-1 4-124 5-1 3-1 5-1 5-1 5-1

In another further preferred embodiment, the invention relates tocompounds of the formula (I′p1)

in which Y is a direct bond and the structural elements R¹, R², R^(3a),R^(3b), R⁴ and R⁵ have the meanings given the following table:

R¹ R² R^(3a), R^(3b) R⁴ R⁵ meaning meaning meaning meaning meaning givenin given in given in given in given in Configu- Configu- Configu-Configu- Configu- entry ration ration ration ration ration 1 4-2 4-2 5-24-2 4-2 2 4-2 4-2 5-2 4-2 5-2 3 4-2 4-2 5-2 5-2 4-2 4 4-2 5-2 5-2 4-24-2 5 4-2 5-2 5-2 5-2 4-2 6 4-2 5-2 5-2 4-2 5-2 7 4-2 4-2 5-2 5-2 5-2 84-2 5-2 5-2 5-2 5-2 9 5-2 4-2 5-2 4-2 4-2 10 5-2 4-2 5-2 4-2 5-2 11 5-24-2 5-2 5-2 4-2 12 5-2 5-2 5-2 4-2 4-2 13 5-2 5-2 5-2 5-2 4-2 14 5-2 5-25-2 4-2 5-2 15 5-2 4-2 5-2 5-2 5-2 16 5-2 5-2 5-2 5-2 5-2 17 4-2 3-2 5-24-2 4-2 18 4-2 3-2 5-2 4-2 5-2 19 4-2 3-2 5-2 5-2 4-2 20 4-2 3-2 5-2 5-25-2 21 5-2 3-2 5-2 4-2 4-2 22 5-2 3-2 5-2 4-2 5-2 23 5-2 3-2 5-2 5-2 4-224 5-2 3-2 5-2 5-2 5-2

In accordance with a further aspect, the present invention coversintermediate compounds which are useful for the preparation of thecompounds of general formula (I), supra.

Particularly, the invention covers the intermediate compounds of generalformula (a*):

in which the structural elements Y, R¹, R², R^(3a) and R^(3b) have themeanings given in Configuration (1-1) or in Configuration (2-1) or inConfiguration (3-1) or in Configuration (4-1) or in Configuration (5-1).

Particularly, the invention also covers the intermediate compounds ofgeneral formula (a*):

in which the structural elements Y, R¹, R², R^(3a) and R^(3b) have themeanings given in Configuration (1-2) or in Configuration (2-2) or inConfiguration (3-2) or in Configuration (4-2) or in Configuration (5-2).

Particularly, the invention covers the intermediate compounds of generalformula (b*):

in which:E is hydrogen or C₁-C₆alkyl;A is —CN, chlorine or fluorine;

L is S, SO or SO₂.

Particularly, the invention covers the intermediate compounds of generalformula (c*):

in which:E is hydrogen or C₁-C₆alkyl;A is bromine, chlorine, fluorine, —CN or trifluoromethyl, preferablychlorine.

Particularly, the invention covers the intermediate compounds of generalformula (d*):

in which:E is hydrogen or C₁-C₆alkyl;A is bromine, chlorine or fluorine, preferably chlorine;L is S, SO or SO₂, preferably S or SO₂, more preferably SO₂;J is ethyl, iso-propyl, tert-butyl, cyclopropyl, 2,2,2-trifluoroethyl or4-fluorophenyl;and wherein the compound of formula (d*) is not3-(ethylsulfanyl)-5-fluorobenzoic acid or3-(tert-butylsulfanyl)-5-fluorobenzoic acid.

The invention also covers the compounds3-cyclopropyl-5-(trifluoromethoxy)benzoic acid and methyl3-cyclopropyl-5-(trifluoromethoxy)benzoate.

The compounds of the formula (I) may possibly also, depending on thenature of the substituents, be in the form of stereoisomers, i.e. in theform of geometric and/or optical isomers or isomer mixtures of varyingcomposition. This invention provides both the pure stereoisomers and anydesired mixtures of these isomers, even though it is generally onlycompounds of the formula (I) that are discussed here.

However, preference is given in accordance with the invention to usingthe optically active, stereoisomeric forms of the compounds of theformula (I) and salts thereof.

The invention therefore relates both to the pure enantiomers anddiastereomers and to mixtures thereof for controlling animal pests,including arthropods and particularly insects.

If appropriate, the compounds of the formula (I) may be present invarious polymorphic forms or as a mixture of various polymorphic forms.Both the pure polymorphs and the polymorph mixtures are provided by theinvention and can be used in accordance with the invention.

DEFINITIONS

The person skilled in the art is aware that, if not stated explicitly,the expressions “a” or “an” as used in the present application may,depending on the situation, mean “one (1)”, “one (1) or more” or “atleast one (1)”.

For all the structures described herein, such as ring systems andgroups, adjacent atoms must not be —O—O— or —O—S—.

Structures having a variable number of possible carbon atoms (C atoms)may be referred to in the present application asC_(lower limit of carbon atoms)—C_(upper limit of carbon atoms)structures (C_(LL)-C_(UL) structures), in order thus to be stipulatedmore specifically. Example: an alkyl group may consist of 3 to 10 carbonatoms and in that case corresponds to C₃-C₁₀alkyl. Ring structurescomposed of carbon atoms and heteroatoms may be referred to as “LL- toUL-membered” structures. One example of a 6-membered ring structure istoluene (a 6-membered ring structure substituted by a methyl group).

If a collective term for a substituent, for example C_(LL)-C_(UL)alkyl,is at the end of a composite substituent, for exampleC_(LL)-C_(UL)cycloalkyl-C_(LL)-C_(UL)alkyl, the constituent at the startof the composite substituent, for example the C_(LL)-C_(UL)cycloalkyl,may be mono- or polysubstituted identically or differently andindependently by the latter substituent, for example C_(LL)-C_(UL)alkyl.All the collective terms used in this application for chemical groups,cyclic systems and cyclic groups can be stipulated more specificallythrough the addition “C_(LL)-C_(UL)” or “LL- to UL-membered”.

In the definitions of the symbols given in the above formulae,collective terms which are generally representative of the followingsubstituents were used:

Halogen relates to elements of the 7th main group, preferably fluorine,chlorine, bromine and iodine, more preferably fluorine, chlorine andbromine, and even more preferably fluorine and chlorine.

Examples of heteroatom are N, O, S, P, B, Si. Preferably, the term“heteroatom” relates to N, S and O.

According to the invention, “alkyl”—on its own or as part of a chemicalgroup—represents straight-chain or branched hydrocarbons preferablyhaving 1 to 6 carbon atoms, for example methyl, ethyl, n-propyl,isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, pentyl, 1-methylbutyl,2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-methylpentyl,2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylpropyl,1,3-dimethylbutyl, 1,4-dimethylbutyl, 2,3-dimethylbutyl,1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl,1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl and2-ethylbutyl. Preference is also given to alkyls having 1 to 4 carbonatoms such as, inter alia, methyl, ethyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, s-butyl or t-butyl. The inventive alkyls may besubstituted by one or more identical or different radicals.

According to the invention, “alkenyl”—on its own or as part of achemical group—represents straight-chain or branched hydrocarbonspreferably having 2 to 6 carbon atoms and at least one double bond, forexample vinyl, 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl,2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl,2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl,2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl,3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl,2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl,1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl,1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 2,2-dimethyl-3-butenyl,2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl,1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl and1-ethyl-2-methyl-2-propenyl. Preference is also given to alkenyls having2 to 4 carbon atoms such as, inter alia, 2-propenyl, 2-butenyl or1-methyl-2-propenyl. The inventive alkenyls may be substituted by one ormore identical or different radicals.

According to the invention, “alkynyl”—on its own or as part of achemical group—represents straight-chain or branched hydrocarbonspreferably having 2 to 6 carbon atoms and at least one triple bond, forexample 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl,2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butynyl,2-methyl-3-butynyl, 1-methyl-2-butynyl, 1,1-dimethyl-2-propynyl,1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl,1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl,2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl,4-methyl-2-pentynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl,2,2-dimethyl-3-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl,1-ethyl-1-methyl-2-propynyl and 2,5-hexadiynyl. Preference is also givento alkynyls having 2 to 4 carbon atoms such as, inter alia, ethynyl,2-propynyl or 2-butynyl-2-propenyl. The inventive alkynyls may besubstituted by one or more identical or different radicals.

According to the invention, “cycloalkyl”—on its own or as part of achemical group—represents mono-, bi- or tricyclic hydrocarbonspreferably having 3 to 10 carbons, for example cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl,bicyclo[2.2.2]octyl or adamantyl. Preference is also given tocycloalkyls having 3, 4, 5, 6 or 7 carbon atoms such as, inter alia,cyclopropyl or cyclobutyl. The inventive cycloalkyls may be substitutedby one or more identical or different radicals.

According to the invention, “alkylcycloalkyl” represents mono-, bi- ortricyclic alkylcycloalkyl preferably having 4 to 10 or 4 to 7 carbonatoms, for example methylcyclopropyl, ethylcyclopropyl,isopropylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl.Preference is also given to alkylcycloalkyls having 4, 5 or 7 carbonatoms such as, inter alia, ethylcyclopropyl or 4-methylcyclohexyl. Theinventive alkylcycloalkyls may be substituted by one or more identicalor different radicals.

According to the invention, “cycloalkylalkyl” represents mono-, bi- ortricyclic cycloalkylalkyl preferably having 4 to 10 or 4 to 7 carbonatoms, for example cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl, cyclohexylmethyl and cyclopentylethyl. Preference isalso given to cycloalkylalkyls having 4, 5 or 7 carbon atoms such as,inter alia, cyclopropylmethyl or cyclobutylmethyl. The inventivecycloalkylalkyls may be substituted by one or more identical ordifferent radicals.

According to the invention, “hydroxyalkyl” represents a straight-chainor branched alcohol preferably having 1 to 6 carbon atoms, for examplemethanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol,s-butanol and t-butanol. Preference is also given to hydroxyalkyl groupshaving 1 to 4 carbon atoms. The inventive hydroxyalkyl groups may besubstituted by one or more identical or different radicals.

According to the invention, “alkoxy” represents a straight-chain orbranched O-alkyl preferably having 1 to 6 carbon atoms, for examplemethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxyand t-butoxy. Preference is also given to alkoxy groups having 1 to 4carbon atoms. The inventive alkoxy groups may be substituted by one ormore identical or different radicals.

According to the invention, “alkylthio”, or “alkylsulfanyl” representsstraight-chain or branched S-alkyl preferably having 1 to 6 carbonatoms, for example methylthio, ethylthio, n-propylthio, isopropylthio,n-butylthio, isobutylthio, s-butylthio and t-butylthio. Preference isalso given to alkylthio groups having 1 to 4 carbon atoms. The inventivealkylthio groups may be substituted by one or more identical ordifferent radicals.

According to the invention, “alkylsulfinyl” represents straight-chain orbranched alkylsulfinyl preferably having 1 to 6 carbon atoms, forexample methylsulfinyl, ethylsulfinyl, n-propylsulfinyl,isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, s-butylsulfinyland t-butylsulfinyl. Preference is also given to alkylsulfinyl groupshaving 1 to 4 carbon atoms. The inventive alkylsulfinyl groups may besubstituted by one or more identical or different radicals and embraceboth enantiomers.

According to the invention, “alkylsulfonyl” represents straight-chain orbranched alkylsulfonyl preferably having 1 to 6 carbon atoms, forexample methylsulfonyl, ethylsulfonyl, n-propylsulfonyl,isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, s-butylsulfonyland t-butylsulfonyl. Preference is also given to alkylsulfonyl groupshaving 1 to 4 carbon atoms. The inventive alkylsulfonyl groups may besubstituted by one or more identical or different radicals.

According to the invention, “cycloalkylthio” or “cycloalkylsulfanyl”represents —S-cycloalkyl preferably having 3 to 6 carbon atoms, forexample cyclopropylthio, cyclobutylthio, cyclopentylthio,cyclohexylthio. Preference is also given to cycloalkylthio groups having3 to 5 carbon atoms. The inventive cycloalkylthio groups may besubstituted by one or more identical or different radicals.

According to the invention, “cycloalkylsulfinyl” represents—S(O)-cycloalkyl preferably having 3 to 6 carbon atoms, for examplecyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl,cyclohexylsulfinyl. Preference is also given to cycloalkylsulfinylgroups having 3 to 5 carbon atoms. The inventive cycloalkylsulfinylgroups may be substituted by one or more identical or different radicalsand embrace both enantiomers.

According to the invention, “cycloalkylsulfonyl” represents—SO₂-cycloalkyl preferably having 3 to 6 carbon atoms, for examplecyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl,cyclohexylsulfonyl. Preference is also given to cycloalkylsulfonylgroups having 3 to 5 carbon atoms. The inventive cycloalkylsulfonylgroups may be substituted by one or more identical or differentradicals.

According to the invention, “phenylthio”, or “phenylsulfanyl” represents—S-phenyl, for example phenylthio. The inventive phenylthio groups maybe substituted by one or more identical or different radicals.

According to the invention, “phenylsulfinyl” represents —S(O)-phenyl,for example phenylsulfinyl. The inventive phenylsulfinyl groups may besubstituted by one or more identical or different radicals and embraceboth enantiomers.

According to the invention, “phenylsulfonyl” represents —SO₂-phenyl forexample phenylsulfonyl. The inventive phenylsulfonyl groups may besubstituted by one or more identical or different radicals.

According to the invention, “alkylcarbonyl” represents straight-chain orbranched alkyl-C(═O) preferably having 2 to 7 carbon atoms such asmethylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl,s-butylcarbonyl and t-butylcarbonyl. Preference is also given toalkylcarbonyls having 1 to 4 carbon atoms. The inventive alkylcarbonylsmay be substituted by one or more identical or different radicals.

According to the invention, “alkoxycarbonyl”−alone or as a constituentof a chemical group−represents straight-chain or branchedalkoxycarbonyl, preferably having 1 to 6 carbon atoms or having 1 to 4carbon atoms in the alkoxy moiety, for example methoxycarbonyl,ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, s-butoxycarbonyland t-butoxycarbonyl. The inventive alkoxycarbonyl groups may besubstituted by one or more identical or different radicals.

According to the invention, “alkylaminocarbonyl” representsstraight-chain or branched alkylaminocarbonyl having preferably 1 to 6carbon atoms or 1 to 4 carbon atoms in the alkyl moiety, for examplemethylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl,isopropylaminocarbonyl, s-butylaminocarbonyl and t-butylaminocarbonyl.The inventive alkylaminocarbonyl groups may be substituted by one ormore identical or different radicals.

According to the invention, “N,N-dialkylaminocarbonyl” representsstraight-chain or branched N,N-dialkylaminocarbonyl having preferably 1to 6 carbon atoms or 1 to 4 carbon atoms in the alkyl moiety, forexample N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl,N,N-di(n-propylamino)carbonyl, N,N-di(isopropylamino)carbonyl andN,N-di-(s-butylamino)carbonyl. The inventive N,N-dialkylaminocarbonylgroups may be substituted by one or more identical or differentradicals.

According to the invention, “aryl” represents a mono-, bi- or polycyclicaromatic system having preferably 6 to 14, especially 6 to 10, ringcarbon atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl,preferably phenyl. In addition, aryl also represents polycyclic systemssuch as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenyl, wherethe bonding site is on the aromatic system. The inventive aryl groupsmay be substituted by one or more identical or different radicals.

Examples of substituted aryls are the arylalkyls, which may likewise besubstituted by one or more identical or different radicals in theC₁-C₄alkyl and/or C₆-C₄aryl moiety. Examples of such arylalkyls includebenzyl and phenyl-1-ethyl.

According to the invention, “heterocycle”, “heterocyclic ring” or“heterocyclic ring system” represents a carbocyclic ring system havingat least one ring in which at least one carbon atom is replaced by aheteroatom, preferably by a heteroatom from the group consisting of N,O, S, P, B, Si, Se, and which is saturated, unsaturated orheteroaromatic and may be unsubstituted or substituted, where thebonding site is on a ring atom. Unless defined differently, theheterocyclic ring contains preferably 3 to 9 ring atoms, especially 3 to6 ring atoms, and one or more, preferably 1 to 4, especially 1, 2 or 3,heteroatoms in the heterocyclic ring, preferably from the groupconsisting of N, O, and S, although no two oxygen atoms should bedirectly adjacent. The heterocyclic rings usually contain not more than4 nitrogen atoms and/or not more than 2 oxygen atoms and/or not morethan 2 sulphur atoms. When the heterocyclyl radical or the heterocyclicring is optionally substituted, it may be fused to other carbocyclic orheterocyclic rings. In the case of optionally substituted heterocyclyl,the invention also embraces polycyclic systems, for example8-azabicyclo[3.2.1]octanyl or 1-azabicyclo[2.2.1]heptyl. In the case ofoptionally substituted heterocyclyl, the invention also embracesspirocyclic systems, for example 1-oxa-5-azaspiro[2.3]hexyl.

Inventive heterocyclyl groups are, for example, piperidinyl,piperazinyl, morpholinyl, thiomorpholinyl, dihydropyranyl,tetrahydropyranyl, dioxanyl, pyrrolinyl, pyrrolidinyl, imidazolinyl,imidazolidinyl, thiazolidinyl, oxazolidinyl, dioxolanyl, dioxolyl,pyrazolidinyl, tetrahydrofuranyl, dihydrofuranyl, oxetanyl, oxiranyl,azetidinyl, aziridinyl, oxazetidinyl, oxaziridinyl, oxazepanyl,oxazinanyl, azepanyl, oxopyrrolidinyl, dioxopyrrolidinyl,oxomorpholinyl, oxopiperazinyl and oxepanyl.

Of particular significance are heteroaryls, i.e. heteroaromatic systems.According to the invention, the term heteroaryl representsheteroaromatic compounds, i.e. completely unsaturated aromaticheterocyclic compounds which fall under the above definition ofheterocycles. Preference is given to 5- to 7-membered rings having 1 to3, preferably 1 or 2, identical or different heteroatoms from the groupabove. Inventive heteroaryls are, for example, furyl, thienyl,pyrazolyl, imidazolyl, 1,2,3- and 1,2,4-triazolyl, isoxazolyl,thiazolyl, isothiazolyl, 1,2,3-, 1,3,4-, 1,2,4- and 1,2,5-oxadiazolyl,azepinyl, pyrrolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl,1,3,5-, 1,2,4- and 1,2,3-triazinyl, 1,2,4-, 1,3,2-, 1,3,6- and1,2,6-oxazinyl, oxepinyl, thiepinyl, 1,2,4-triazolonyl and1,2,4-diazepinyl. The inventive heteroaryl groups may also besubstituted by one or more identical or different radicals.

The term “in each case optionally substituted” means that agroup/substituent, such as a alkyl, alkenyl, alkynyl, alkoxy, alkylthio,alkylsulfinyl, alkylsulfonyl, cycloalkyl, aryl, phenyl, benzyl,heterocyclyl and heteroaryl radical, is substituted, meaning, forexample, a substituted radical derived from the unsubstituted basestructure, where the substituents, for example, one (1) substituent or aplurality of substituents, preferably 1, 2, 3, 4, 5, 6 or 7, areselected from a group consisting of amino, hydroxyl, halogen, nitro,cyano, isocyano, mercapto, isothiocyanato, C₁-C₄carboxyl, carbonamide,SF₅, aminosulphonyl, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₄cycloalkyl,C₂-C₄alkenyl, C₅-C₆cycloalkenyl, C₂-C₄alkynyl, N-mono-C₁-C₄alkylamino,N,N-di-C₁-C₄alkylamino, N—C₁-C₄alkanoylamino, C₁-C₄alkoxy,C₁-C₄haloalkoxy, C₂-C₄alkenyloxy, C₂-C₄alkynyloxy, C₃-C₄cycloalkoxy,C₅-C₆cycloalkenyloxy, C₁-C₄alkoxycarbonyl, C₂-C₄alkenyloxycarbonyl,C₂-C₄alkynyloxycarbonyl, C₆—, C₁₀—, C₁₄-aryloxycarbonyl, C₁-C₄alkanoyl,C₂-C₄alkenylcarbonyl, C₂-C₄alkynylcarbonyl, C₆—, C₁₀—, C₁₄-arylcarbonyl,C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₃-C₄cycloalkylthio,C₂-C₄alkenylthio, C₅-C₆cycloalkenylthio, C₂-C₄alkynylthio,C₁-C₄alkylsulfinyl, including both enantiomers of the C₁-C₄alkylsulfinylgroup, C₁-C₄haloalkylsulfinyl, including both enantiomers of theC₁-C₄haloalkylsulfinyl group, C₁-C₄alkylsulfonyl,C₁-C₄haloalkylsulfonyl, N-mono-C₁-C₄alkylaminosulfonyl,N,N-di-C₁-C₄alkylaminosulfonyl, C₁-C₄alkylphosphinyl,C₁-C₄alkylphosphonyl, including both enantiomers of C₁-C₄alkylphosphinyland C₁-C₄alkylphosphonyl, N—C₁-C₄alkylaminocarbonyl,N,N-di-C₁-C₄alkylaminocarbonyl, N—C₁-C₄alkanoylaminocarbonyl,N—C₁-C₄alkanoyl-N—C₁-C₄alkylaminocarbonyl, C₆—, C₁₀—, C₁₄-aryl, C₆—,C₁₀—, C₁₄-aryloxy, benzyl, benzyloxy, benzylthio, C₆—, C₁₀—,C₁₄-arylthio, C₆—, C₁₀—, C₁₄-arylamino, benzylamino, heterocyclyl andtrialkylsilyl, substituents bonded via a double bond, such asC₁-C₄alkylidene (e.g. methylidene or ethylidene), an oxo group, an iminogroup and a substituted imino group. When two or more radicals form oneor more rings, these may be carbocyclic, heterocyclic, saturated, partlysaturated, unsaturated, for example including aromatic rings and withfurther substitution. The substituents mentioned by way of example(“first substituent level”) may, if they contain hydrocarbonaceouscomponents, optionally have further substitution therein (“secondsubstituent level”), for example by one or more of the substituents eachindependently selected from halogen, hydroxyl, amino, nitro, cyano,isocyano, azido, acylamino, an oxo group and an imino group. The term“(optionally) substituted” group preferably embraces just one or twosubstituent levels.

The inventive halogen-substituted chemical groups or halogenated groups(for example alkyl or alkoxy) are mono- or polysubstituted by halogen upto the maximum possible number of substituents. Such groups are alsoreferred to as halo groups (for example haloalkyl). In the case ofpolysubstitution by halogen, the halogen atoms may be the same ordifferent, and may all be bonded to one carbon atom or may be bonded toa plurality of carbon atoms. Halogen is especially fluorine, chlorine,bromine or iodine, preferably fluorine, chlorine or bromine and morepreferably fluorine. More particularly, halogen-substituted groups aremonohalocycloalkyl such as 1-fluorocyclopropyl, 2-fluorocyclopropyl or1-fluorocyclobutyl, monohaloalkyl such as 2-chloroethyl, 2-fluoroethyl,1-chloroethyl, 1-fluoroethyl, chloromethyl, or fluoromethyl;perhaloalkyl such as trichloromethyl or trifluoromethyl or CF₂CF₃,polyhaloalkyl such as difluoromethyl, 2-fluoro-2-chloroethyl,dichloromethyl, 1,1,2,2-tetrafluoroethyl or 2,2,2-trifluoroethyl.Further examples of haloalkyls are trichloromethyl,chlorodifluoromethyl, dichlorofluoromethyl, chloromethyl, bromomethyl,1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2,2,2-trichloroethyl, 2-chloro-2,2-difluoroethyl, pentafluoroethyl,3,3,3-trifluoropropyl and pentafluoro-t-butyl. Preference is given tohaloalkyls having 1 to 4 carbon atoms and 1 to 9, preferably 1 to 5,identical or different halogen atoms selected from fluorine, chlorineand bromine. Particular preference is given to haloalkyls having 1 or 2carbon atoms and 1 to 5 identical or different halogen atoms selectedfrom fluorine and chlorine, such as, inter alia, difluoromethyl,trifluoromethyl or 2,2-difluoroethyl. Further examples ofhalogen-substituted compounds are haloalkoxy such as OCF₃, OCHF₂, OCH₂F,OCF₂CF₃, OCH₂CF₃, OCH₂CHF₂ und OCH₂CH₂Cl₁, haloalkylsulfanyls such asdifluoromethylthio, trifluoromethylthio, trichloromethylthio,chlorodifluoromethylthio, 1-fluoroethylthio, 2-fluoroethylthio,2,2-difluoroethylthio, 1,1,2,2-tetrafluoroethylthio,2,2,2-trifluoroethylthio or 2-chloro-1,1,2-trifluoroethylthio,haloalkylsulfinyls such as difluoromethylsulfinyl,trifluoromethylsulfinyl, trichloromethylsulfinyl,chlorodifluoromethylsulfinyl, 1-fluoroethylsulfinyl,2-fluoroethylsulfinyl, 2,2-difluoroethylsulfinyl,1,1,2,2-tetrafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl and2-chloro-1,1,2-trifluoroethylsulfinyl, haloalkylsulfinyls such asdifluoromethylsulfinyl, trifluoromethylsulfinyl,trichloromethylsulfinyl, chlorodifluoromethylsulfinyl,1-fluoroethylsulfinyl, 2-fluoroethylsulfinyl, 2,2-difluoroethylsulfinyl,1,1,2,2-tetrafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl and2-chloro-1,1,2-trifluoroethylsulfinyl, haloalkylsulfonyl groups such asdifluoromethylsulfonyl, trifluoromethylsulfonyl,trichloromethylsulfonyl, chlorodifluoromethylsulfonyl,1-fluoroethylsulfonyl, 2-fluoroethylsulfonyl, 2,2-difluoroethylsulfonyl,1,1,2,2-tetrafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl and2-chloro-1,1,2-trifluoroethylsulfonyl.

In the case of radicals having carbon atoms, preference is given tothose having 1 to 4 carbon atoms, especially 1 or 2 carbon atoms.Preference is generally given to substituents from the group of halogen,e.g. fluorine and chlorine, (C₁-C₄)alkyl, preferably methyl or ethyl,(C₁-C₄)haloalkyl, preferably trifluoromethyl, (C₁-C₄)alkoxy, preferablymethoxy or ethoxy, (C₁-C₄)haloalkoxy, nitro and cyano. Particularpreference is given here to the substituents methyl, methoxy, fluorineand chlorine.

Substituted amino such as mono- or disubstituted amino means a radicalfrom the group of the substituted amino radicals which areN-substituted, for example, by one or two identical or differentradicals from the group of alkyl, hydroxy, amino, alkoxy, acyl and aryl;preferably N-mono- and N,N-dialkylamino, (for example methylamino,ethylamino, N,N-dimethylamino, N,N-diethylamino, N,N-di-n-propylamino,N,N-diisopropylamino or N,N-dibutylamino), N-mono- orN,N-dialkoxyalkylamino groups (for example N-methoxymethylamino,N-methoxyethylamino, N,N-di(methoxymethyl)amino orN,N-di(methoxyethyl)amino), N-mono- and N,N-diarylamino, such asoptionally substituted anilines, acylamino, N,N-diacylamino,N-alkyl-N-arylamino, N-alkyl-N-acylamino and also saturatedN-heterocycles; preference is given here to alkyl radicals having 1 to 4carbon atoms; here, aryl is preferably phenyl or substituted phenyl; foracyl, the definition given further below applies, preferably(C₁-C₄)-alkanoyl. The same applies to substituted hydroxylamino orhydrazino.

Substituted amino also includes quaternary ammonium compounds (salts)having four organic substituents on the nitrogen atom.

Optionally substituted phenyl is preferably phenyl which isunsubstituted or mono- or polysubstituted, preferably up totrisubstituted, by identical or different radicals from the group ofhalogen, (C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy,(C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulfinyl (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl (C₁-C₄)haloalkylsulfonyl, cyano,isocyano and nitro, for example o-, m- and p-tolyl, dimethylphenyls, 2-,3- and 4-chlorophenyl, 2-, 3- and 4-fluorophenyl, 2-, 3- and4-trifluoromethyl- and 4-trichloromethylphenyl, 2,4-, 3,5-, 2,5- and2,3-dichlorophenyl, o-, m- and p-methoxyphenyl, 4-heptafluorophenyl.

Optionally substituted cycloalkyl is preferably cycloalkyl which isunsubstituted or mono- or polysubstituted, preferably up totrisubstituted, by identical or different radicals from the group ofhalogen, cyano, (C₁-C₄)alkyl, (C₁-C₄)alkoxy,(C₁-C₄)alkoxy-(C₁-C₄)alkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₁-C₄)haloalkyl and (C₁-C₄)haloalkoxy, especially by one or two(C₁-C₄)alkyl radicals.

Inventive compounds may occur in preferred embodiments. Individualembodiments described herein may be combined with one another. Notincluded are combinations which contravene the laws of nature and whichthe person skilled in the art would therefore rule out on the basis ofhis/her expert knowledge. Ring structures having three or more adjacentoxygen atoms, for example, are excluded.

Isomers

Depending on the nature of the substituents, the compounds of theformula (I) may be in the form of geometric and/or optically activeisomers or corresponding isomer mixtures in different compositions.These stereoisomers are, for example, enantiomers, diastereomers,atropisomers or geometric isomers. Accordingly, the inventionencompasses both pure stereoisomers and any mixture of these isomers.

Methods and Uses

The invention also relates to methods for controlling animal pests, inwhich compounds of the formula (I) are allowed to act on animal pestsand/or their habitat. The control of the animal pests is preferablyconducted in agriculture and forestry, and in material protection.Preferably excluded herefrom are methods for the surgical or therapeutictreatment of the human or animal body and diagnostic methods carried outon the human or animal body.

The invention furthermore relates to the use of the compounds of theformula (I) as pesticides, in particular crop protection agents.

In the context of the present application, the term “pesticide” in eachcase also always comprises the term “crop protection agent”.

The compounds of the formula (I), having good plant tolerance,favourable homeotherm toxicity and good environmental compatibility, aresuitable for protecting plants and plant organs against biotic andabiotic stressors, for increasing harvest yields, for improving thequality of the harvested material and for controlling animal pests,especially insects, arachnids, helminths, in particular nematodes, andmolluscs, which are encountered in agriculture, in horticulture, inanimal husbandry, in aquatic cultures, in forests, in gardens andleisure facilities, in the protection of stored products and ofmaterials, and in the hygiene sector.

Within the context of the present patent application, the term “hygiene”is understood to mean any and all measures, procedures and practiceswhich aim to prevent disease, in particular infectious disease, andwhich serve to protect the health of humans and animals and/or toprotect the environment, and/or which maintain cleanliness. Inaccordance with the invention, this especially includes measures forcleaning, disinfection and sterilisation of, for example, textiles orhard surfaces, especially surfaces of glass, wood, concrete, porcelain,ceramics, plastic or also of metal(s), and for ensuring that these arekept free of hygiene pests and/or their excretions. Preferably excludedfrom the scope of the invention in this regard are surgical ortherapeutic treatment procedures applicable to the human body or to thebodies of animals and diagnostic procedures which are carried out on thehuman body or on the bodies of animals.

The term “hygiene sector” thus covers all areas, technical fields andindustrial applications in which these hygiene measures, procedures andpractices are important, in relation for example to hygiene in kitchens,bakeries, airports, bathrooms, swimming pools, department stores,hotels, hospitals, stables, animal husbandries, etc.

The term “hygiene pest” is therefore understood to mean one or moreanimal pests whose presence in the hygiene sector is problematic, inparticular for health reasons. It is therefore a primary objective toavoid or minimize the presence of hygiene pests, and/or exposure tothem, in the hygiene sector. This can be achieved in particular throughthe application of a pesticide that can be used both to preventinfestation and to tackle an infestation which is already present.Preparations which avoid or reduce exposure to pests can also be used.Hygiene pests include, for example, the organisms mentioned below.

The term “hygiene protection” thus covers all actions to maintain and/orimprove these hygiene measures, procedures and practices.

The compounds of the formula (I) can preferably be used as pesticides.They are active against normally sensitive and resistant species andagainst all or some stages of development. The abovementioned pestsinclude:

pests from the phylum of the Arthropoda, in particular from the class ofthe Arachnida, for example Acarus spp., for example Acarus siro, Aceriakuko, Aceria sheldoni, Aculops spp., Aculus spp., for example Aculusfockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychusviennensis, Argas spp., Boophilus spp., Brevipalpus spp., for exampleBrevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroidesspp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoidespteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychusspp., for example Eotetranychus hicoriae, Epitrimerus pyri,Eutetranychus spp., for example Eutetranychus banksi, Eriophyes spp.,for example Eriophyes pyri, Glycyphagus domesticus, Halotydeusdestructor, Hemitarsonemus spp., for example Hemitarsonemus latus(=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectusspp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp.,Oligonychus spp., for example Oligonychus coffeae, Oligonychusconiferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychusmangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychusyothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., forexample Panonychus citri (=Metatetranychus citri), Panonychus ulmi(=Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychusmultidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalusspp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus,Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., forexample Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., forexample Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychusturkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp.,Vasates lycopersici;from the class of the Chilopoda, for example Geophilus spp., Scutigeraspp.;from the order or the class of the Collembola, for example Onychiurusarmatus; Sminthurus viridis;from the class of the Diplopoda, for example Blaniulus guttulatus;from the class of the Insecta, for example from the order of theBlattodea, for example Blatta orientalis, Blattella asahinai, Blattellagermanica, Leucophaea maderae, Loboptera decipiens, Neostylopygarhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., forexample Periplaneta americana, Periplaneta australasiae, Pycnoscelussurinamensis, Supella longipalpa;from the order of the Coleoptera, for example Acalymma vittatum,Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelasticaalni, Agrilus spp., for example Agrilus planipennis, Agrilus coxalis,Agrilus bilineatus, Agrilus anxius, Agriotes spp., for example Agrioteslinneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallonsolstitialis, Anobium punctatum, Anoplophora spp., for exampleAnoplophora glabripennis, Anthonomus spp., for example Anthonomusgrandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., forexample Atomaria linearis, Attagenus spp., Baris caerulescens,Bruchidius obtectus, Bruchus spp., for example Bruchus pisorum, Bruchusrufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., forexample Ceutorrhynchus assimilis, Ceutorrhynchus quadridens,Ceutorrhynchus rapae, Chaetocnema spp., for example Chaetocnemaconfinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus,Conoderus spp., Cosmopolites spp., for example Cosmopolites sordidus,Costelytra zealandica, Ctenicera spp., Curculio spp., for exampleCurculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi,Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi,Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturusadspersus, Cylindrocopturus furnissi, Dendroctonus spp., for exampleDendroctonus ponderosae, Dermestes spp., Diabrotica spp., for exampleDiabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctatahowardi, Diabrotica undecimpunctata undecimpunctata, Diabroticavirgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp.,Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp.,for example Epilachna borealis, Epilachna varivestis, Epitrix spp., forexample Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrixsubcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides,Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyxspp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomecessquamosus, Hypothenemus spp., for example Hypothenemus hampei,Hypothenemus obscurus, Hypothenemus pubescens, Lachnosternaconsanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp.,Lema spp., Leptinotarsa decemlineata, Leucoptera spp., for exampleLeucoptera coffeella, Limonius ectypus, Lissorhoptrus oryzophilus,Listronotus (=Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorphaxanthodera, Lyctus spp., Megacyllene spp., for example Megacyllenerobiniae, Megascelis spp., Melanotus spp., for example Melanotuslongulus oregonensis, Meligethes aeneus, Melolontha spp., for exampleMelolontha melolontha, Migdolus spp., Monochamus spp., Naupactusxanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus,Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae,Otiorhynchus spp., for example Otiorhynchus cribricollis, Otiorhynchusligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus,Otiorhynchus sulcatus, Oulema spp., for example Oulema melanopus, Oulemaoryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp.,Phyllophaga helleri, Phyllotreta spp., for example Phyllotretaarmoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotretastriolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus,Psylliodes spp., for example Psylliodes affinis, Psylliodeschrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis,Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferrugineus,Rhynchophorus palmarum, Scolytus spp., for example Scolytusmultistriatus, Sinoxylon perforans, Sitophilus spp., for exampleSitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophiluszeamais, Sphenophorus spp., Stegobium paniceum, Sternechus spp., forexample Sternechus paludatus, Symphyletes spp., Tanymecus spp., forexample Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus,Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., for exampleTribolium audax, Tribolium castaneum, Tribolium confusum, Trogodermaspp., Tychius spp., Xylotrechus spp., Zabrus spp., for example Zabrustenebrioides;from the order of the Dermaptera, for example Anisolabis maritime,Forficula auricularia, Labidura riparia;from the order of the Diptera, for example Aedes spp., for example Aedesaegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp.,for example Agromyza frontella, Agromyza parvicornis, Anastrepha spp.,Anopheles spp., for example Anopheles quadrimaculatus, Anophelesgambiae, Asphondylia spp., Bactrocera spp., for example Bactroceracucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus,Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata,Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis,Cochliomya spp., Contarinia spp., for example Contarinia johnsoni,Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi,Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga,Cricotopus sylvestris, Culex spp., for example Culex pipiens, Culexquinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacusoleae, Dasineura spp., for example Dasineura brassicae, Delia spp., forexample Delia antiqua, Delia coarctata, Delia florilega, Delia platura,Delia radicum, Dermatobia hominis, Drosophila spp., for exampleDrosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleiaheraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopotaspp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp.,Hypoderma spp., Liriomyza spp., for example Liriomyza brassicae,Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., for exampleLucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp., for exampleMusca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit,Paratanytarsus spp., Paralauterborniella subcincta, Pegomya or Pegomyiaspp., for example Pegomya betae, Pegomya hyoscyami, Pegomya rubivora,Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platypareapoeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., forexample Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta,Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella,Sarcophaga spp., Simulium spp., for example Simulium meridionale,Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., for exampleTipula paludosa, Tipula simplex, Toxotrypana curvicauda;from the order of the Hemiptera, for example Acizzia acaciaebaileyanae,Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosiponspp., for example Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp.,Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobusbarodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrascaspp., for example Amrasca bigutulla, Amrasca devastans, Anuraphiscardui, Aonidiella spp., for example Aonidiella aurantii, Aonidiellacitrina, Aonidiella inornata, Aphanostigma piri, Aphis spp., for exampleAphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphisglycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphismiddletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola,Aphis viburniphila, Arboridia apicalis, Arytainilla spp., Aspidiellaspp., Aspidiotus spp., for example Aspidiotus nerii, Atanus spp.,Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis,Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp.,Brevicoryne brassicae, Cacopsylla spp., for example Cacopsylla pyricola,Calligypona marginata, Capulinia spp., Carneocephala fulgida,Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphonfragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea,Chromaphis juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus,Cicadulina mbila, Coccomytilus halli, Coccus spp., for example Coccushesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis,Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp.,Dialeurodes chittendeni, Dialeurodes citri, Diaphorina citri, Diaspisspp., Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., forexample Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae,Dysmicoccus spp., Empoasca spp., for example Empoasca abrupta, Empoascafabae, Empoasca maligna, Empoasca solana, Empoasca stevensi, Eriosomaspp., for example Eriosoma americanum, Eriosoma lanigerum, Eriosomapyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp.,Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica,Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsyllaspinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopteruspruni, Icerya spp., for example Icerya purchasi, Idiocerus spp.,Idioscopus spp., Laodelphax striatellus, Lecanium spp., for exampleLecanium corni (=Parthenolecanium corni), Lepidosaphes spp., for exampleLepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycormadelicatula, Macrosiphum spp., for example Macrosiphum euphorbiae,Macrosiphum lilii, Macrosiphum rosae, Macrosteles facifrons, Mahanarvaspp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa,Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzusspp., for example Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzusornatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri,Neomaskellia spp., Nephotettix spp., for example Nephotettix cincticeps,Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens,Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp.,Parabemisia myricae, Paratrioza spp., for example Paratrioza cockerelli,Parlatoria spp., Pemphigus spp., for example Pemphigus bursarius,Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccusspp., for example Phenacoccus madeirensis, Phloeomyzus passerinii,Phorodon humuli, Phylloxera spp., for example Phylloxera devastatrix,Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., forexample Planococcus citri, Prosopidopsylla flava, Protopulvinariapyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., for examplePseudococcus calceolariae, Pseudococcus comstocki, Pseudococcuslongispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsisspp., Psylla spp., for example Psylla buxi, Psylla mali, Psylla pyri,Pteromalus spp., Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp.,for example Quadraspidiotus juglansregiae, Quadraspidiotusostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcusspp., Rhopalosiphum spp., for example Rhopalosiphum maidis,Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphumrufiabdominale, Saissetia spp., for example Saissetia coffeae, Saissetiamiranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus,Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobionavenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephalafestina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephelaspp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., forexample Toxoptera aurantii, Toxoptera citricidus, Trialeurodesvaporariorum, Trioza spp., for example Trioza diospyri, Typhlocyba spp.,Unaspis spp., Viteus vitifolii, Zygina spp.; from the suborder of theHeteroptera, for example Aelia spp., Anasa tristis, Antestiopsis spp.,Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Caveleriusspp., Cimex spp., for example Cimex adjunctus, Cimex hemipterus, Cimexlectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus,Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercusspp., Euschistus spp., for example Euschistus heros, Euschistus servus,Euschistus tristigmus, Euschistus variolarius, Eurydema spp., Eurygasterspp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus,Leptocorisa spp., Leptocorisa varicornis, Leptoglossus occidentalis,Leptoglossus phyllopus, Lygocoris spp., for example Lygocoris pabulinus,Lygus spp., for example Lygus elisus, Lygus hesperus, Lygus lineolaris,Macropes excavatus, Megacopta cribraria, Miridae, Monalonion atratum,Nezara spp., for example Nezara viridula, Nysius spp., Oebalus spp.,Pentomidae, Piesma quadrata, Piezodorus spp., for example Piezodorusguildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergellasingularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi,Tibraca spp., Triatoma spp.;from the order of the Hymenoptera, for example Acromyrmex spp., Athaliaspp., for example Athalia rosae, Atta spp., Camponotus spp.,Dolichovespula spp., Diprion spp., for example Diprion similis,Hoplocampa spp., for example Hoplocampa cookei, Hoplocampa testudinea,Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis,Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., forexample Sirex noctilio, Solenopsis invicta, Tapinoma spp., Technomyrmexalbipes, Urocerus spp., Vespa spp., for example Vespa crabro, Wasmanniaauropunctata, Xeris spp.; from the order of the Isopoda, for exampleArmadillidium vulgare, Oniscus asellus, Porcellio scaber;from the order of the Isoptera, for example Coptotermes spp., forexample Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp.,Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermesspp., Odontotermes spp., Porotermes spp., Reticulitermes spp., forexample Reticulitermes flavipes, Reticulitermes hesperus;from the order of the Lepidoptera, for example Achroia grisella,Acronicta major, Adoxophyes spp., for example Adoxophyes orana, Aedialeucomelas, Agrotis spp., for example Agrotis segetum, Agrotis ipsilon,Alabama spp., for example Alabama argillacea, Amyelois transitella,Anarsia spp., Anticarsia spp., for example Anticarsia gemmatalis,Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra,Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseolaspp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsapomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., forexample Chilo plejadellus, Chilo suppressalis, Choreutis pariana,Choristoneura spp., Chrysodeixis chalcites, Clysia ambiguella,Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp.,Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., forexample Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphaniaspp., Diparopsis spp., Diatraea saccharalis, Dioryctria spp., forexample Dioryctria zimmermani, Earias spp., Ecdytolopha aurantium,Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., for exampleEphestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyaspostvittana, Erannis spp., Erschoviella musculana, Etiella spp.,Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., forexample Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleriamellonella, Gracillaria spp., Grapholitha spp., for example Grapholitamolesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., forexample Helicoverpa armigera, Helicoverpa zea, Heliothis spp., forexample Heliothis virescens, Hofmannophila pseudospretella, Homoeosomaspp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata,Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis,Leucoptera spp., for example Leucoptera coffeella, Lithocolletis spp.,for example Lithocolletis blancardella, Lithophane antennata, Lobesiaspp., for example Lobesia botrana, Loxagrotis albicosta, Lymantria spp.,for example Lymantria dispar, Lyonetia spp., for example Lyonetiaclerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae,Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata,Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp.,Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., for exampleOstrinia nubilalis, Panolis flammea, Parnara spp., Pectinophora spp.,for example Pectinophora gossypiella, Perileucoptera spp., Phthorimaeaspp., for example Phthorimaea operculella, Phyllocnistis citrella,Phyllonorycter spp., for example Phyllonorycter blancardella,Phyllonorycter crataegella, Pieris spp., for example Pieris rapae,Platynota stultana, Plodia interpunctella, Plusia spp., Plutellaxylostella (=Plutella maculipennis), Podesia spp., for example Podesiasyringae, Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp.,for example Pseudaletia unipuncta, Pseudoplusia includens, Pyraustanubilalis, Rachiplusia nu, Schoenobius spp., for example Schoenobiusbipunctifer, Scirpophaga spp., for example Scirpophaga innotata, Scotiasegetum, Sesamia spp., for example Sesamia inferens, Sparganothis spp.,Spodoptera spp., for example Spodoptera eradiana, Spodoptera exigua,Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenomaspp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora,Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tineapellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella,Trichoplusia spp., for example Trichoplusia ni, Tryporyza incertulas,Tuta absoluta, Virachola spp.;from the order of the Orthoptera or Saltatoria, for example Achetadomesticus, Dichroplus spp., Gryllotalpa spp., for example Gryllotalpagryllotalpa, Hieroglyphus spp., Locusta spp., for example Locustamigratoria, Melanoplus spp., for example Melanoplus devastator,Paratlanticus ussuriensis, Schistocerca gregaria;from the order of the Phthiraptera, for example Damalinia spp.,Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxeravastatrix, Phthirus pubis, Trichodectes spp.;from the order of the Psocoptera, for example Lepinotus spp., Liposcelisspp.;from the order of the Siphonaptera, for example, Ceratophyllus spp.,Ctenocephalides spp., for example Ctenocephalides canis, Ctenocephalidesfelis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis;from the order of the Thysanoptera, for example Anaphothrips obscurus,Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri,Enneothrips flavens, Frankliniella spp., for example Frankliniellafusca, Frankliniella occidentalis, Frankliniella schultzei,Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi,Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothripsspp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothripscardamomi, Thrips spp., for example Thrips palmi, Thrips tabaci;from the order of the Zygentoma (=Thysanura), for example Ctenolepismaspp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica;from the class of the Symphyla, for example Scutigerella spp., forexample Scutigerella immaculata; pests from the phylum of the Mollusca,for example from the class of the Bivalvia, for example Dreissena spp.,and also from the class of the Gastropoda, for example Arion spp., forexample Arion ater rufus, Biomphalaria spp., Bulinus spp., Derocerasspp., for example Deroceras laeve, Galba spp., Lymnaea spp., Oncomelaniaspp., Pomacea spp., Succinea spp.;plant pests from the phylum of the Nematoda, i.e. phytoparasiticnematodes, in particular Aglenchus spp., for example Aglenchus agricola,Anguina spp., for example Anguina tritici, Aphelenchoides spp., forexample Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimusspp., for example Belonolaimus gracilis, Belonolaimus longicaudatus,Belonolaimus nortoni, Bursaphelenchus spp., for example Bursaphelenchuscocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus,Cacopaurus spp., for example Cacopaurus pestis, Criconemella spp., forexample Criconemella curvata, Criconemella onoensis, Criconemellaornata, Criconemella rusium, Criconemella xenoplax (=Mesocriconemaxenoplax), Criconemoides spp., for example Criconemoides ferniae,Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., forexample Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., forexample Globodera pallida, Globodera rostochiensis, Helicotylenchusspp., for example Helicotylenchus dihystera, Hemicriconemoides spp.,Hemicycliophora spp., Heterodera spp., for example Heterodera avenae,Heterodera glycines, Heterodera schachtii, Hirschmaniella spp.,Hoplolaimus spp., Longidorus spp., for example Longidorus africanus,Meloidogyne spp., for example Meloidogyne chitwoodi, Meloidogyne fallax,Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp.,Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp.,Paratrichodorus spp., for example Paratrichodorus minor, Paratylenchusspp., Pratylenchus spp., for example Pratylenchus penetrans,Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulciusspp., Radopholus spp., for example Radopholus citrophilus, Radopholussimilis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp.,Subanguina spp., Trichodorus spp., for example Trichodorus obtusus,Trichodorus primitivus, Tylenchorhynchus spp., for exampleTylenchorhynchus annulatus, Tylenchulus spp., for example Tylenchulussemipenetrans, Xiphinema spp., for example Xiphinema index.

The compounds of the formula (I) can optionally, at certainconcentrations or application rates, also be used as herbicides,safeners, growth regulators or agents to improve plant properties, asmicrobicides or gametocides, for example as fungicides, antimycotics,bactericides, viricides (including agents against viroids) or as agentsagainst MLO (mycoplasma-like organisms) and RLO (rickettsia-likeorganisms). If appropriate, they can also be used as intermediates orprecursors for the synthesis of other active compounds.

Formulations

The present invention further relates to formulations and use formsprepared therefrom as pesticides, for example drench, drip and sprayliquors, comprising at least one compound of the formula (I). In somecases, the use forms comprise further pesticides and/or adjuvants whichimprove action, such as penetrants, e.g. vegetable oils, for examplerapeseed oil, sunflower oil, mineral oils, for example paraffin oils,alkyl esters of vegetable fatty acids, for example rapeseed oil methylester or soya oil methyl ester, or alkanol alkoxylates and/or spreaders,for example alkylsiloxanes and/or salts, for example organic orinorganic ammonium or phosphonium salts, for example ammonium sulphateor diammonium hydrogenphosphate and/or retention promoters, for exampledioctyl sulphosuccinate or hydroxypropyl guar polymers and/orhumectants, for example glycerol and/or fertilizers, for exampleammonium-, potassium- or phosphorus-containing fertilizers.

Customary formulations are, for example, water-soluble liquids (SL),emulsion concentrates (EC), emulsions in water (EW), suspensionconcentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules(GR) and capsule concentrates (CS); these and further possibleformulation types are described, for example, by Crop Life Internationaland in Pesticide Specifications, Manual on development and use of FAOand WHO specifications for pesticides, FAO Plant Production andProtection Papers−173, prepared by the FAO/WHO Joint Meeting onPesticide Specifications, 2004, ISBN: 9251048576. The formulations, inaddition to one or more compounds of the formula (I), optionallycomprise further agrochemically active compounds.

These are preferably formulations or use forms which compriseauxiliaries, for example extenders, solvents, spontaneity promoters,carriers, emulsifiers, dispersants, frost protectants, biocides,thickeners and/or further auxiliaries, for example adjuvants. Anadjuvant in this context is a component which enhances the biologicaleffect of the formulation, without the component itself having anybiological effect. Examples of adjuvants are agents which promoteretention, spreading, attachment to the leaf surface or penetration.

These formulations are prepared in a known way, for example by mixingthe compounds of the formula (I) with auxiliaries such as, for example,extenders, solvents and/or solid carriers and/or other auxiliaries suchas, for example, surfactants. The formulations are prepared either insuitable facilities or else before or during application.

The auxiliaries used may be substances suitable for imparting specialproperties, such as certain physical, technical and/or biologicalproperties, to the formulation of the compounds of the formula (I), orto the use forms prepared from these formulations (for exampleready-to-use pesticides such as spray liquors or seed dressingproducts).

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), the esters (including fats andoils) and (poly)ethers, the unsubstituted and substituted amines,amides, lactams (such as N-alkylpyrrolidones) and lactones, thesulphones and sulphoxides (such as dimethyl sulphoxide), the carbonatesand the nitriles.

If the extender used is water, it is also possible to employ, forexample, organic solvents as auxiliary solvents. Essentially, suitableliquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample mineral oil fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide or dimethylsulphoxide, carbonates such as propylene carbonate, butylene carbonate,diethyl carbonate or dibutyl carbonate, or nitriles such as acetonitrileor propanenitrile.

In principle, it is possible to use all suitable solvents. Examples ofsuitable solvents are aromatic hydrocarbons, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatic or chlorinated aliphatichydrocarbons, such as chlorobenzene, chloroethylene or methylenechloride, aliphatic hydrocarbons, such as cyclohexane, paraffins,petroleum fractions, mineral and vegetable oils, alcohols, such asmethanol, ethanol, isopropanol, butanol or glycol and their ethers andesters, ketones such as acetone, methyl ethyl ketone, methyl isobutylketone or cyclohexanone, strongly polar solvents, such as dimethylsulphoxide, carbonates such as propylene carbonate, butylene carbonate,diethyl carbonate or dibutyl carbonate, nitriles such as acetonitrile orpropanenitrile, and also water.

In principle, it is possible to use all suitable carriers. Usefulcarriers include especially: for example ammonium salts and groundnatural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticmaterials such as finely divided silica, alumina and natural orsynthetic silicates, resins, waxes and/or solid fertilizers. Mixtures ofsuch carriers can likewise be used. Useful carriers for granulesinclude: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite, dolomite, and synthetic granules ofinorganic and organic meals, and also granules of organic material suchas sawdust, paper, coconut shells, corn cobs and tobacco stalks.

Liquefied gaseous extenders or solvents can also be used. Particularlysuitable extenders or carriers are those which are gaseous at ambienttemperature and under atmospheric pressure, for example aerosolpropellant gases, such as halohydrocarbons, and also butane, propane,nitrogen and carbon dioxide.

Examples of emulsifiers and/or foam-formers, dispersants or wettingagents with ionic or nonionic properties, or mixtures of thesesurfactants, are salts of polyacrylic acid, salts of lignosulphonicacid, salts of phenolsulphonic acid or naphthalenesulphonic acid,polycondensates of ethylene oxide with fatty alcohols or with fattyacids or with fatty amines, with substituted phenols (preferablyalkylphenols or arylphenols), salts of sulphosuccinic esters, taurinederivatives (preferably alkyl taurates), isethionate derivatives,phosphoric esters of polyethoxylated alcohols or phenols, fatty estersof polyols, and derivatives of the compounds containing sulphates,sulphonates and phosphates, for example alkylaryl polyglycol ethers,alkylsulphonates, alkyl sulphates, arylsulphonates, proteinhydrolysates, lignosulphite waste liquors and methylcellulose. Thepresence of a surfactant is advantageous if one of the compounds of theformula (I) and/or one of the inert carriers is insoluble in water andwhen the application takes place in water.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyes such asalizarin dyes, azo dyes and metal phthalocyanine dyes, and nutrients andtrace nutrients such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc as further auxiliaries in the formulations and theuse forms derived therefrom.

Additional components may be stabilizers, such as low-temperaturestabilizers, preservatives, antioxidants, light stabilizers or otheragents which improve chemical and/or physical stability. Foam formers orantifoams may also be present.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids may also be present as additional auxiliaries in theformulations and the use forms derived therefrom. Further possibleauxiliaries are mineral and vegetable oils.

Optionally, further auxiliaries may be present in the formulations andthe use forms derived therefrom. Examples of such additives includefragrances, protective colloids, binders, adhesives, thickeners,thixotropic agents, penetrants, retention promoters, stabilizers,sequestrants, complexing agents, humectants, spreaders. In general, thecompounds of the formula (I) can be combined with any solid or liquidadditive commonly used for formulation purposes.

Useful retention promoters include all those substances which reduce thedynamic surface tension, for example dioctyl sulphosuccinate, orincrease the viscoelasticity, for example hydroxypropylguar polymers.

Suitable penetrants in the present context are all those substanceswhich are usually used for improving the penetration of agrochemicalactive compounds into plants. Penetrants are defined in this context bytheir ability to penetrate from the (generally aqueous) applicationliquor and/or from the spray coating into the cuticle of the plant andthereby increase the mobility of active compounds in the cuticle. Themethod described in the literature (Baur et al., 1997, Pesticide Science51, 131-152) can be used to determine this property. Examples includealcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecylethoxylate (12), fatty acid esters, for example rapeseed oil methylester or soya oil methyl ester, fatty amine alkoxylates, for exampletallowamine ethoxylate (15), or ammonium and/or phosphonium salts, forexample ammonium sulphate or diammonium hydrogenphosphate.

The formulations preferably comprise between 0.00000001 and 98% byweight of the compound of the formula (I) or, with particularpreference, between 0.01% and 95% by weight of the compound of theformula (I), more preferably between 0.5% and 90% by weight of thecompound of the formula (I), based on the weight of the formulation.

The content of the compound of the formula (I) in the use forms preparedfrom the formulations (in particular pesticides) may vary within wideranges. The concentration of the compound of the formula (I) in the useforms is usually between 0.00000001 and 95% by weight of the compound ofthe formula (I), preferably between 0.00001 and 1% by weight, based onthe weight of the use form. The compounds are employed in a customarymanner appropriate for the use forms.

Mixtures

The compounds of the formula (I) may also be employed as a mixture withone or more suitable fungicides, bactericides, acaricides,molluscicides, nematicides, insecticides, microbiologicals, beneficialspecies, herbicides, fertilizers, bird repellents, phytotonics,sterilants, safeners, semiochemicals and/or plant growth regulators, inorder thus, for example, to broaden the spectrum of action, to prolongthe duration of action, to increase the rate of action, to preventrepulsion or prevent evolution of resistance. In addition, such activecompound combinations may improve plant growth and/or tolerance toabiotic factors, for example high or low temperatures, to drought or toelevated water content or soil salinity. It is also possible to improveflowering and fruiting performance, optimize germination capacity androot development, facilitate harvesting and improve yields, influencematuration, improve the quality and/or the nutritional value of theharvested products, prolong storage life and/or improve theprocessability of the harvested products.

Furthermore, the compounds of the formula (I) can be present in amixture with other active compounds or semiochemicals such asattractants and/or bird repellants and/or plant activators and/or growthregulators and/or fertilizers. Likewise, the compounds of the formula(I) can be used to improve plant properties such as, for example,growth, yield and quality of the harvested material.

In a particular embodiment according to the invention, the compounds ofthe formula (I) are present in formulations or the use forms preparedfrom these formulations in a mixture with further compounds, preferablythose as described below.

If one of the compounds mentioned below can occur in differenttautomeric forms, these forms are also included even if not explicitlymentioned in each case. Further, all named mixing partners can, if theirfunctional groups enable this, optionally form salts with suitable basesor acids.

Insecticides/Acaricides/Nematicides

The active compounds identified here by their common names are known andare described, for example, in the pesticide handbook (“The PesticideManual” 16th Ed., British Crop Protection Council 2012) or can be foundon the Internet (e.g. http://www.alanwood.net/pesticides). Theclassification is based on the current IRAC Mode of ActionClassification Scheme at the time of filing of this patent application.

(1) Acetylcholinesterase (AChE) inhibitors, preferably carbamatesselected from alanycarb, aldicarb, bendiocarb, benfuracarb,butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan,ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb,methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur,thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb, ororganophosphates selected from acephate, azamethiphos, azinphos-ethyl,azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos,chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos,demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate,dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur,fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos,isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate,isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos,monocrotophos, naled, omethoate, oxydemeton-methyl, parathion-methyl,phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos,pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos,tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion.(2) GABA-gated chloride channel blockers, preferablycyclodiene-organochlorines selected from chlordane and endosulfan orphenylpyrazoles (fiproles), for example ethiprole and fipronil.(3) Sodium channel modulators, preferably pyrethroids selected fromacrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin,bifenthrin, bioallethrin, bioallethrin s-cyclopentenyl isomer,bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin,lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin,beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin[(1R)-trans-isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer],esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate,flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin,momfluorothrin, permethrin, phenothrin [(1R)-trans-isomer], prallethrin,pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin,tetramethrin, tetramethrin [(1R)-isomer)], tralomethrin andtransfluthrin or DDT or methoxychlor.(4) Nicotinic acetylcholine receptor (nAChR) competitive modulators,preferably neonicotinoids selected from acetamiprid, clothianidin,dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam ornicotine or sulfoxaflor or flupyradifurone.(5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators,preferably spinosyns selected from spinetoram and spinosad.(6) Glutamate-gated chloride channel (GluCl) allosteric modulators,preferably avermectins/milbemycins selected from abamectin, emamectinbenzoate, lepimectin and milbemectin.(7) Juvenile hormone mimics, preferably juvenile hormone analoguesselected from hydroprene, kinoprene and methoprene, or fenoxycarb orpyriproxyfen.(8) Miscellaneous non-specific (multi-site) inhibitors, preferably alkylhalides selected from methyl bromide and other alkyl halides, orchloropicrine or sulphuryl fluoride or borax or tartar emetic or methylisocyanate generators selected from diazomet and metam.(9) Chordotonal organ TRPV channel modulators selected from pymetrozineand pyrifluquinazone.(10) Mite growth inhibitors selected from clofentezine, hexythiazox,diflovidazin and etoxazole.(11) Microbial disruptors of the insect gut membrane selected fromBacillus thuringiensis subspecies israelensis, Bacillus sphaericus,Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensissubspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, andB.t. plant proteins selected from Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105,Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb and Cry34Ab1/35Ab1.(12) Inhibitors of mitochondrial ATP synthase, preferably ATP disruptorsselected from diafenthiuron, or organotin compounds selected fromazocyclotin, cyhexatin and fenbutatin oxide, or propargite ortetradifon.(13) Uncouplers of oxidative phosphorylation via disruption of theproton gradient selected from chlorfenapyr, DNOC and sulfluramid.(14) Nicotinic acetylcholine receptor channel blockers selected frombensultap, cartap hydrochloride, thiocylam and thiosultap-sodium.(15) Inhibitors of chitin biosynthesis, type 0, selected frombistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron,teflubenzuron and triflumuron.(16) Inhibitors of chitin biosynthesis, type 1 selected from buprofezin.(17) Moulting disruptor (in particular for Diptera, i.e. dipterans)selected from cyromazine.(18) Ecdysone receptor agonists selected from chromafenozide,halofenozide, methoxyfenozide and tebufenozide.(19) Octopamine receptor agonists selected from amitraz.(20) Mitochondrial complex III electron transport inhibitors selectedfrom hydramethylnone, acequinocyl and fluacrypyrim.(21) Mitochondrial complex I electron transport inhibitors, preferablyMETI acaricides selected from fenazaquin, fenpyroximate, pyrimidifen,pyridaben, tebufenpyrad and tolfenpyrad, or rotenone (Derris).(22) Voltage-dependent sodium channel blockers selected from indoxacarband metaflumizone.(23) Inhibitors of acetyl CoA carboxylase, preferably tetronic andtetramic acid derivatives selected from spirodiclofen, spiromesifen andspirotetramat.(24) Mitochondrial complex IV electron transport inhibitors, preferablyphosphines selected from aluminium phosphide, calcium phosphide,phosphine and zinc phosphide, or cyanides selected from calcium cyanide,potassium cyanide and sodium cyanide.(25) Mitochondrial complex II electron transport inhibitors, preferablybeta-ketonitrile derivatives selected from cyenopyrafen andcyflumetofen, and carboxanilides selected from pyflubumide.(28) Ryanodine receptor modulators, preferably diamides selected fromchlorantraniliprole, cyantraniliprole and flubendiamide.(29) Chordotonal organ Modulators (with undefined target site) selectedfrom flonicamid.(30) further active compounds selected from Acynonapyr, Afidopyropen,Afoxolaner, Azadirachtin, Benclothiaz, Benzoximate, Benzpyrimoxan,Bifenazate, Broflanilide, Bromopropylate, Chinomethionat,Chloroprallethrin, Cryolite, Cyclaniliprole, Cycloxaprid, Cyhalodiamide,Dicloromezotiaz, Dicofol, epsilon-Metofluthrin, epsilon-Momfluthrin,Flometoquin, Fluazaindolizine, Fluensulfone, Flufenerim,Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Flupyrimin,Fluralaner, Fluxametamide, Fufenozide, Guadipyr, Heptafluthrin,Imidaclothiz, Iprodione, kappa-Bifenthrin, kappa-Tefluthrin, Lotilaner,Meperfluthrin, Oxazosulfyl, Paichongding, Pyridalyl, Pyrifluquinazon,Pyriminostrobin, Spirobudiclofen, Spiropidion, Tetramethylfluthrin,Tetraniliprole, Tetrachlorantraniliprole, Tigolaner, Tioxazafen,Thiofluoximate, Triflumezopyrim and iodomethane; furthermorepreparations based on Bacillus firmus (I-1582, BioNeem, Votivo), andalso the following compounds:1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine(known from WO2006/043635) (CAS 885026-50-6),{1′-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indol-3,4′-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone(known from WO2003/106457) (CAS 637360-23-7),2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide(known from WO2006/003494) (CAS 872999-66-1),3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one(known from WO 2010052161) (CAS 1225292-17-0),3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethyl carbonate (known from EP2647626) (CAS 1440516-42-6),4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine(known from WO2004/099160) (CAS 792914-58-0), PF1364 (known fromJP2010/018586) (CAS 1204776-60-2),(3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoro-propan-2-one(known from WO2013/144213) (CAS 1461743-15-6),N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide(known from WO2010/051926) (CAS 1226889-14-0),5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide(known from CN103232431) (CAS 1449220-44-3),4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)-benzamide,4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxido-3-thietanyl)-benzamideand4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide(known from WO 2013/050317 A1) (CAS 1332628-83-7),N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide,(+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamideand(−)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide(known from WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 A1)(CAS 1477923-37-7),5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile(known from CN 101337937 A) (CAS 1105672-77-2),3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thioxomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide,(Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9);N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-Pyrazole-5-carboxamide(known from WO 2012/034403 A1) (CAS 1268277-22-0),N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide(known from WO 2011/085575 A1) (CAS 1233882-22-8),4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)-pyrimidine(known from CN 101337940 A) (CAS 1108184-52-6); (2E)- and2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide(known from CN 101715774 A) (CAS 1232543-85-9);3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl-cyclopropanecarboxylicacid ester (known from CN 103524422 A) (CAS 1542271-46-4);(4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]-indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylicacid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2);6-deoxy-3-O-ethyl-2,4-di-O-methyl-,1-[N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-3-yl]phenyl]carbamate]-α-L-mannopyranose(known from US 2014/0275503 A1) (CAS 1181213-14-8);8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane(CAS 1253850-56-4),(8-anti)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane(CAS933798-27-7),(8-syn)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane(known from WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8),N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]-propanamide(known from WO 2015/058021 A1, WO 2015/058028 A1) (CAS 1477919-27-9) andN-[4-(aminothioxomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide(known from CN 103265527 A) (CAS 1452877-50-7),5-(1,3-dioxan-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]-pyrimidine(known from WO 2013/115391 A1) (CAS 1449021-97-9),3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazaspiro[4.5]decane-2,4-dione(known from WO 2014/187846 A1) (CAS 1638765-58-8),3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl-carbonicacid ethyl ester (known from WO 2010/066780 A1, WO 2011151146 A1) (CAS1229023-00-0),4-[(5S)-5-(3,5-Dichloro-4-fluorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[(4R)-2-ethyl-3-oxo-4-isoxazolidinyl]-2-methyl-benzamide(bekannt aus WO 2011/067272, WO2013/050302) (CAS 1309959-62-3).

Fungicides

The active ingredients specified herein by their Common Name are knownand described, for example, in The Pesticide Manual (16th Ed.BritishCrop Protection Council) or can be searched in the internet (e.g.www.alanwood.net/pesticides).

All named fungicidal mixing partners of the classes (1) to (15) can, iftheir functional groups enable this, optionally form salts with suitablebases or acids. All named mixing partners of the classes (1) to (15) caninclude tautomeric forms, where applicable.

1) Inhibitors of the ergosterol biosynthesis, for example (1.001)cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004)fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007)fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010)imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013)metconazole, (1.014) myclobutanil, (1.015) paclobutrazol, (1.016)prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019)Pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022)tetraconazole, (1.023) triadimenol, (1.024) tridemorph, (1.025)triticonazole, (1.026)(1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.027)(1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.028)(2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.029)(2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.030)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.031)(2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.032)(2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.033)(2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.034)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.035)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.036)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.037)1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole,(1.038)1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole,(1.039)1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.040)1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.041)1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.042)2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.043)2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.044)2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.045)2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.046)2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.047)2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.048)2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.049)2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.050)2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.051)2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.052)2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.053)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.054)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol,(1.055)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.056)2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.057)2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.058)2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.059)5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.060)5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.061)5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.062)5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.063)N′-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.064)N′-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.065)N′-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.066)N′-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.067)N′-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.068)N′-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.069)N′-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.070)N′-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.071)N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide,(1.072)N′-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(1.073)N′-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(1.074)N′-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide,(1.075)N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide,(1.076)N′-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.077)N′-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.078)N′-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.079)N′-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.080)N′-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.081) Mefentrifluconazole, (1.082) Ipfentrifluconazole.2) Inhibitors of the respiratory chain at complex I or II, for example(2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004)carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad,(2.008) furametpyr, (2.009) Isofetamid, (2.010) isopyrazam(anti-epimeric enantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimericenantiomer 1S,4R,9R), (2.012) isopyrazam (anti-epimeric racemate1RS,4SR,9SR), (2.013) isopyrazam (mixture of syn-epimeric racemate1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (2.014) isopyrazam(syn-epimeric enantiomer 1R,4S,9R), (2.015) isopyrazam (syn-epimericenantiomer 1S,4R,9S), (2.016) isopyrazam (syn-epimeric racemate1RS,4SR,9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019)pydiflumetofen, (2.020) Pyraziflumid, (2.021) sedaxane, (2.022)1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.023)1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.024)1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.025)1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(2.026)2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide,(2.027)3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.028)3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.029)3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.030)3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide,(2.031)3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.032)3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.033)5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine,(2.034)N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.035)N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.036)N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.037)N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.038)N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.039)N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.040)N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.041)N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.042)N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.043)N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.044)N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.045)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide,(2.046)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.047)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.048)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide,(2.049)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.050)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.051)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.052)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-H-pyrazole-4-carboxamide,(2.053)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.054)N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.055)N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.056)N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide.3) Inhibitors of the respiratory chain at complex III, for example(3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004)coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007)dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010)fenamidone, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013)kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016)picoxystrobin, (3.017) pyraclostrobin, (3.018) pyrametostrobin, (3.019)pyraoxystrobin, (3.020) trifloxystrobin, (3.021)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide,(3.022)(2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide,(3.023)(2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.024)(2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.025)(3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl2-methylpropanoate, (3.026)2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.027)N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide,(3.028)(2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide,(3.029) methyl{5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate.4) Inhibitors of the mitosis and cell division, for example (4.001)carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004)fluopicolide, (4.005) pencycuron, (4.006) thiabendazole, (4.007)thiophanate-methyl, (4.008) zoxamide, (4.009)3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, (4.010)3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,(4.011)3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine,(4.012)4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.013)4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.014)4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.015)4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.016)4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.017)4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.018)4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.019)4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.020)4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.021)4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.022)₄-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,(4.023)N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.024)N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.025)N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine.5) Compounds capable to have a multisite action, for example (5.001)bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004)chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate,(5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper(2+)sulfate, (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013)mancozeb, (5.014) maneb, (5.015) metiram, (5.016) metiram zinc, (5.017)oxine-copper, (5.018) propineb, (5.019) sulfur and sulfur preparationsincluding calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022)ziram, (5.023)6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3′,4′:5,6][1,4]dithiino[2,3-c][1,2]thiazole-3-carbonitrile.6) Compounds capable to induce a host defence, for example (6.001)acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004)tiadinil.7) Inhibitors of the amino acid and/or protein biosynthesis, for example(7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycinhydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil,(7.006)3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline.8) Inhibitors of the ATP production, for example (8.001) silthiofam.9) Inhibitors of the cell wall synthesis, for example (9.001)benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004)iprovalicarb, (9.005) mandipropamid, (9.006) pyrimorph, (9.007)valifenalate, (9.008)(2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(9.009)(2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.10) Inhibitors of the lipid and membrane synthesis, for example (10.001)propamocarb, (10.002) propamocarb hydrochloride, (10.003)tolclofos-methyl.11) Inhibitors of the melanin biosynthesis, for example (11.001)tricyclazole, (11.002) 2,2,2-trifluoroethyl{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.12) Inhibitors of the nucleic acid synthesis, for example (12.001)benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl,(12.004) metalaxyl-M (mefenoxam).13) Inhibitors of the signal transduction, for example (13.001)fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004)proquinazid, (13.005) quinoxyfen, (13.006) vinclozolin.14) Compounds capable to act as an uncoupler, for example (14.001)fluazinam, (14.002) meptyldinocap.15) Further compounds, for example (15.001) Abscisic acid, (15.002)benthiazole, (15.003) bethoxazin, (15.004) capsimycin, (15.005) carvone,(15.006) chinomethionat, (15.007) cufraneb, (15.008) cyflufenamid,(15.009) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil,(15.012) fosetyl-aluminium, (15.013) fosetyl-calcium, (15.014)fosetyl-sodium, (15.015) methyl isothiocyanate, (15.016) metrafenone,(15.017) mildiomycin, (15.018) natamycin, (15.019) nickeldimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021)oxamocarb, (15.022) Oxathiapiprolin, (15.023) oxyfenthiin, (15.024)pentachlorophenol and salts, (15.025) phosphorous acid and its salts,(15.026) propamocarb-fosetylate, (15.027) pyriofenone (chlazafenone),(15.028) tebufloquin, (15.029) tecloftalam, (15.030) tolnifanide,(15.031)1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.032)1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methy-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034)2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone,(15.035)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.036)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.037)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.038)2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline,(15.039)2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (15.040)2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (15.041)2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol,(15.042)2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol,(15.043)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (15.044)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethanesulfonate, (15.045) 2-phenylphenol and salts, (15.046)3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.047)3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form:4-amino-5-fluoropyrimidin-2(1H)-one), (15.049)4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.050)5-amino-1,3,4-thiadiazole-2-thiol, (15.051)5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene-2-sulfonohydrazide,(15.052) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053)5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054)9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine,(15.055) but-3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.056) ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.057)phenazine-1-carboxylic acid, (15.058) propyl 3,4,5-trihydroxybenzoate,(15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2:1), (15.061)tert-butyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.062)5-fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(1H)-one.

Biological Pesticides as Mixing Components

The compounds of the formula (I) can be combined with biologicalpesticides.

Biological pesticides comprise in particular bacteria, fungi, yeasts,plant extracts and products formed by microorganisms, including proteinsand secondary metabolites.

Biological pesticides comprise bacteria such as spore-forming bacteria,root-colonising bacteria and bacteria which act as biologicalinsecticides, fungicides or nematicides.

Examples of such bacteria which are employed or can be used asbiological pesticides are:

Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacilluscereus, in particular B. cereus strain CNCM I-1562 or Bacillus firmus,strain I-1582 (Accession number CNCM I-1582) or Bacillus pumilus, inparticular strain GB34 (Accession No. ATCC 700814) and strain QST2808(Accession No. NRRL B-30087), or Bacillus subtilis, in particular strainGB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713(Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002(Accession No. NRRL B-50421) Bacillus thuringiensis, in particular B.thuringiensis subspecies israelensis (serotype H-14), strain AM65-52(Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, inparticular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp.kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulusreniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomycesmicroflavus strain AQ6121 (=QRD 31.013, NRRL B-50550), Streptomycesgalbus strain AQ 6047 (Acession Number NRRL 30232).

Examples of fungi and yeasts which are employed or can be used asbiological pesticides are: Beauveria bassiana, in particular strain ATCC74040, Coniothyrium minitans, in particular strain CON/M/91-8 (AccessionNo. DSM-9660), Lecanicillium spp., in particular strain HRO LEC 12,Lecanicillium lecanii, (formerly known as Verticillium lecanii), inparticular strain KVO1, Metarhizium anisopliae, in particular strain F52(DSM3884/ATCC 90448), Metschnikowia fructicola, in particular strainNRRL Y-30752, Paecilomyces fumosoroseus (now: Isaria fumosorosea), inparticular strain IFPC 200613, or strain Apopka 97 (Accession No. ATCC20874), Paecilomyces lilacinus, in particular P. lilacinus strain 251(AGAL 89/030550), Talaromyces flavus, in particular strain V117b,Trichoderma atroviride, in particular strain SC (Accession Number CBS122089), Trichoderma harzianum, in particular T. harzianum rifai T39.(Accession Number CNCM I-952).

Examples of viruses which are employed or can be used as biologicalpesticides are: Adoxophyes orana (summer fruit tortrix) granulosis virus(GV), Cydia pomonella (codling moth) granulosis virus (GV), Helicoverpaarmigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodopteraexigua (beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV,Spodoptera littoralis (African cotton leafworm) NPV.

Also included are bacteria and fungi which are added as ‘inoculant’ toplants or plant parts or plant organs and which, by virtue of theirparticular properties, promote plant growth and plant health.

Examples which may be mentioned are:

Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp.,Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particularBurkholderia cepacia (formerly known as Pseudomonas cepacia), Gigasporaspp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillusbuchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp.,Rhizobium spp., in particular Rhizobium trifolii, Rhizopogon spp.,Scleroderma spp., Suillus spp., Streptomyces spp.

Examples of plant extracts and products formed by microorganismsincluding proteins and secondary metabolites which are employed or canbe used as biological pesticides are:

Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassianigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin,Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza,Fungastop, Heads Up (Chenopodium quinoa saponin extract),Pyrethrum/Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia,“Requiem™ Insecticide”, rotenone, ryania/ryanodine, Symphytumofficinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulummajus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extract, inparticular oilseed rape powder or mustard powder.

Safener as Mixing Components

The compounds of the formula (I) can be combined with safeners such as,for example, benoxacor, cloquintocet (-mexyl), cyometrinil,cyprosulfamide, dichlormid, fenchlorazole (-ethyl), fenclorim,flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr(-diethyl), naphthalic anhydride, oxabetrinil,2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulphonyl)benzamide (CAS129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS52836-31-4).

Plants and Plant Parts

All plants and plant parts can be treated in accordance with theinvention. Here, plants are to be understood to mean all plants andplant parts such as wanted and unwanted wild plants or crop plants(including naturally occurring crop plants), for example cereals (wheat,rice, triticale, barley, rye, oats), maize, soya bean, potato, sugarbeet, sugar cane, tomatoes, pepper, cucumber, melon, carrot, watermelon,onion, lettuce, spinach, leek, beans, Brassica oleracea (e.g. cabbage)and other vegetable species, cotton, tobacco, oilseed rape, and alsofruit plants (with the fruits apples, pears, citrus fruits andgrapevines). Crop plants can be plants which can be obtained byconventional breeding and optimization methods or by biotechnologicaland genetic engineering methods or combinations of these methods,including the transgenic plants and including the plant varieties whichcan or cannot be protected by varietal property rights. Plants should beunderstood to mean all developmental stages, such as seeds, seedlings,young (immature) plants up to mature plants. Plant parts should beunderstood to mean all parts and organs of the plants above and belowground, such as shoot, leaf, flower and root, examples given beingleaves, needles, stalks, stems, flowers, fruit bodies, fruits and seeds,and also tubers, roots and rhizomes. Parts of plants also includeharvested plants or harvested plant parts and vegetative and generativepropagation material, for example seedlings, tubers, rhizomes, cuttingsand seeds.

Treatment according to the invention of the plants and plant parts withthe compounds of the formula (I) is carried out directly or by allowingthe compounds to act on the surroundings, environment or storage spaceby the customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on, injection and, in thecase of propagation material, in particular in the case of seeds, alsoby applying one or more coats.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andalso parts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(genetically modified organisms), and parts thereof are treated. Theterm “parts” or “parts of plants” or “plant parts” has been explainedabove. The invention is used with particular preference to treat plantsof the respective commercially customary cultivars or those that are inuse. Plant cultivars are to be understood as meaning plants having newproperties (“traits”) and which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. They can becultivars, varieties, bio- or genotypes.

Transgenic Plant, Seed Treatment and Integration Events

The transgenic plants or plant cultivars (those obtained by geneticengineering) which are to be treated with preference in accordance withthe invention include all plants which, through the geneticmodification, received genetic material which imparts particularadvantageous useful properties (“traits”) to these plants. Examples ofsuch properties are better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to levels of wateror soil salinity, enhanced flowering performance, easier harvesting,accelerated ripening, higher yields, higher quality and/or a highernutritional value of the harvested products, better storage life and/orprocessability of the harvested products. Further and particularlyemphasized examples of such properties are increased resistance of theplants against animal and microbial pests, such as against insects,arachnids, nematodes, mites, slugs and snails owing, for example, totoxins formed in the plants, in particular those formed in the plants bythe genetic material from Bacillus thuringiensis (for example by thegenes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9cCry2Ab, Cry3Bb and CryIF and also combinations thereof), furthermoreincreased resistance of the plants against phytopathogenic fungi,bacteria and/or viruses owing, for example, to systemic acquiredresistance (SAR), systemin, phytoalexins, elicitors and also resistancegenes and correspondingly expressed proteins and toxins, and alsoincreased tolerance of the plants to certain herbicidally activecompounds, for example imidazolinones, sulphonylureas, glyphosate orphosphinothricin (for example the “PAT” gene). The genes which impartthe desired traits in question may also be present in combinations withone another in the transgenic plants. Examples of transgenic plantswhich may be mentioned are the important crop plants, such as cereals(wheat, rice, triticale, barley, rye, oats), maize, soya beans,potatoes, sugar beet, sugar cane, tomatoes, peas and other types ofvegetable, cotton, tobacco, oilseed rape and also fruit plants (with thefruits apples, pears, citrus fruits and grapes), with particularemphasis being given to maize, soya beans, wheat, rice, potatoes,cotton, sugar cane, tobacco and oilseed rape. Traits which areparticularly emphasized are the increased resistance of the plants toinsects, arachnids, nematodes and slugs and snails.

Crop Protection−Types of Treatment

The treatment of the plants and plant parts with the compounds of theformula (I) is carried out directly or by action on their surroundings,habitat or storage space using customary treatment methods, for exampleby dipping, spraying, atomizing, irrigating, evaporating, dusting,fogging, broadcasting, foaming, painting, spreading-on, injecting,watering (drenching), drip irrigating and, in the case of propagationmaterial, in particular in the case of seed, furthermore as a powder fordry seed treatment, a solution for liquid seed treatment, awater-soluble powder for slurry treatment, by incrusting, by coatingwith one or more coats, etc. It is furthermore possible to apply thecompounds of the formula (I) by the ultra-low volume method or to injectthe application form or the compound of the formula (I) itself into thesoil.

A preferred direct treatment of the plants is foliar application, i.e.the compounds of the formula (I) are applied to the foliage, wheretreatment frequency and the application rate should be adjustedaccording to the level of infestation with the pest in question.

In the case of systemically active compounds, the compounds of theformula (I) also access the plants via the root system. The plants arethen treated by the action of the compounds of the formula (I) on thehabitat of the plant. This may be done, for example, by drenching, or bymixing into the soil or the nutrient solution, i.e. the locus of theplant (e.g. soil or hydroponic systems) is impregnated with a liquidform of the compounds of the formula (I), or by soil application, i.e.the compounds of the formula (I) according to the invention areintroduced in solid form (e.g. in the form of granules) into the locusof the plants, or by drip application (often also referred to as“chemigation”), i.e. the liquid application of the compounds of theformula (I) according to the invention from surface or sub-surfacedriplines over a certain period of time together with varying amounts ofwater at defined locations in the vicinity of the plants. In the case ofpaddy rice crops, this can also be done by metering the compound of theformula (I) in a solid application form (for example as granules) into aflooded paddy field.

Treatment of Seed

The control of animal pests by treating the seed of plants has beenknown for a long time and is the subject of continuous improvements.However, the treatment of seed entails a series of problems which cannotalways be solved in a satisfactory manner. Thus, it is desirable todevelop methods for protecting the seed and the germinating plant whichdispense with, or at least reduce considerably, the additionalapplication of pesticides during storage, after sowing or afteremergence of the plants. It is furthermore desirable to optimize theamount of active compound employed in such a way as to provide optimumprotection for the seed and the germinating plant from attack by animalpests, but without damaging the plant itself by the active compoundemployed. In particular, methods for the treatment of seed should alsotake into consideration the intrinsic insecticidal or nematicidalproperties of pest-resistant or -tolerant transgenic plants in order toachieve optimum protection of the seed and also the germinating plantwith a minimum of pesticides being employed.

The present invention therefore in particular also relates to a methodfor the protection of seed and germinating plants, from attack by pests,by treating the seed with one of the compounds of the formula (I). Themethod according to the invention for protecting seed and germinatingplants against attack by pests furthermore comprises a method where theseed is treated simultaneously in one operation or sequentially with acompound of the formula (I) and a mixing component. It also comprises amethod where the seed is treated at different times with a compound ofthe formula (I) and a mixing component.

The invention likewise relates to the use of the compounds of theformula (I) for the treatment of seed for protecting the seed and theresulting plant from animal pests.

Furthermore, the invention relates to seed which has been treated with acompound of the formula (I) according to the invention so as to affordprotection from animal pests. The invention also relates to seed whichhas been treated simultaneously with a compound of the formula (I) and amixing component. The invention furthermore relates to seed which hasbeen treated at different times with a compound of the formula (I) and amixing component. In the case of seed which has been treated atdifferent points in time with a compound of the formula (I) and a mixingcomponent, the individual substances may be present on the seed indifferent layers. Here, the layers comprising a compound of the formula(I) and mixing components may optionally be separated by an intermediatelayer. The invention also relates to seed where a compound of theformula (I) and a mixing component have been applied as component of acoating or as a further layer or further layers in addition to acoating.

Furthermore, the invention relates to seed which, after the treatmentwith a compound of the formula (I), is subjected to a film-coatingprocess to prevent dust abrasion on the seed.

One of the advantages encountered with a systemically acting compound ofthe formula (I) is the fact that, by treating the seed, not only theseed itself but also the plants resulting therefrom are, afteremergence, protected against animal pests. In this manner, the immediatetreatment of the crop at the time of sowing or shortly thereafter can bedispensed with.

It has to be considered a further advantage that by treatment of theseed with a compound of the formula (I), germination and emergence ofthe treated seed may be enhanced.

It is likewise to be considered advantageous that compounds of theformula (I) can be used in particular also for transgenic seed.

Furthermore, compounds of the formula (I) can be employed in combinationwith compositions or compounds of signalling technology, leading tobetter colonization by symbionts such as, for example, rhizobia,mycorrhizae and/or endophytic bacteria or fungi, and/or to optimizednitrogen fixation.

The compounds of the formula (I) are suitable for protection of seed ofany plant variety which is used in agriculture, in the greenhouse, inforests or in horticulture. In particular, this takes the form of seedof cereals (for example wheat, barley, rye, millet and oats), corn,cotton, soya beans, rice, potatoes, sunflowers, coffee, tobacco, canola,oilseed rape, beets (for example sugarbeets and fodder beets), peanuts,vegetables (for example tomatoes, cucumbers, bean, cruciferousvegetables, onions and lettuce), fruit plants, lawns and ornamentalplants. The treatment of the seed of cereals (such as wheat, barley, ryeand oats), maize, soya beans, cotton, canola, oilseed rape, vegetablesand rice is of particular importance.

As already mentioned above, the treatment of transgenic seed with acompound of the formula (I) is also of particular importance. This takesthe form of seed of plants which, as a rule, comprise at least oneheterologous gene which governs the expression of a polypeptide with inparticular insecticidal and/or nematicidal properties. The heterologousgenes in transgenic seed can originate from microorganisms such asBacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter,Glomus or Gliocladium. The present invention is particularly suitablefor the treatment of transgenic seed which comprises at least oneheterologous gene originating from Bacillus sp. It is particularlypreferably a heterologous gene derived from Bacillus thuringiensis.

In the context of the present invention, the compound of the formula (I)is applied to the seed. Preferably, the seed is treated in a state inwhich it is stable enough to avoid damage during treatment. In general,the seed may be treated at any point in time between harvest and sowing.The seed usually used has been separated from the plant and freed fromcobs, shells, stalks, coats, hairs or the flesh of the fruits. Forexample, it is possible to use seed which has been harvested, cleanedand dried down to a moisture content which allows storage.Alternatively, it is also possible to use seed which, after drying, hasbeen treated with, for example, water and then dried again, for examplepriming. In the case of rice seed, it is also possible to use seed whichhas been soaked, for example in water to a certain stage of the riceembryo (‘pigeon breast stage’), stimulating the germination and a moreuniform emergence.

When treating the seed, care must generally be taken that the amount ofthe compound of the formula (I) applied to the seed and/or the amount offurther additives is chosen in such a way that the germination of theseed is not adversely affected, or that the resulting plant is notdamaged. This must be ensured particularly in the case of activecompounds which can exhibit phytotoxic effects at certain applicationrates.

In general, the compounds of the formula (I) are applied to the seed ina suitable formulation. Suitable formulations and processes for seedtreatment are known to the person skilled in the art.

The compounds of the formula (I) can be converted to the customary seeddressing formulations, such as solutions, emulsions, suspensions,powders, foams, slurries or other coating compositions for seed, andalso ULV formulations.

These formulations are prepared in a known manner, by mixing thecompounds of the formula (I) with customary additives such as, forexample, customary extenders and also solvents or diluents, colorants,wetting agents, dispersants, emulsifiers, antifoams, preservatives,secondary thickeners, adhesives, gibberellins and also water.

Colorants which may be present in the seed-dressing formulations whichcan be used in accordance with the invention are all colorants which arecustomary for such purposes. It is possible to use either pigments,which are sparingly soluble in water, or dyes, which are soluble inwater. Examples include the dyes known by the names Rhodamine B, C.I.Pigment Red 112 and C.I. Solvent Red 1.

Useful wetting agents which may be present in the seed dressingformulations usable in accordance with the invention are all substanceswhich promote wetting and which are conventionally used for theformulation of agrochemically active compounds. Preference is given tousing alkylnaphthalenesulphonates, such as diisopropyl- ordiisobutylnaphthalenesulphonates.

Useful dispersants and/or emulsifiers which may be present in the seeddressing formulations usable in accordance with the invention are allnonionic, anionic and cationic dispersants conventionally used for theformulation of active agrochemical ingredients. Preference is given tousing nonionic or anionic dispersants or mixtures of nonionic or anionicdispersants. Suitable nonionic dispersants include in particularethylene oxide/propylene oxide block polymers, alkylphenol polyglycolethers and tristryrylphenol polyglycol ethers, and the phosphated orsulphated derivatives thereof. Suitable anionic dispersants are inparticular lignosulphonates, polyacrylic acid salts andarylsulphonate/formaldehyde condensates.

Antifoams which may be present in the seed dressing formulations usablein accordance with the invention are all foam-inhibiting substancesconventionally used for the formulation of active agrochemicalingredients. Preference is given to using silicone antifoams andmagnesium stearate.

Preservatives which may be present in the seed dressing formulationsusable in accordance with the invention are all substances usable forsuch purposes in agrochemical compositions. Examples includedichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed dressingformulations usable in accordance with the invention are all substanceswhich can be used for such purposes in agrochemical compositions.Cellulose derivatives, acrylic acid derivatives, xanthan, modified claysand finely divided silica are preferred.

Adhesives which may be present in the seed dressing formulations usablein accordance with the invention are all customary binders usable inseed dressing products. Polyvinylpyrrolidone, polyvinyl acetate,polyvinyl alcohol and tylose may be mentioned as being preferred.

Gibberellins which can be present in the seed-dressing formulationswhich can be used in accordance with the invention are preferably thegibberellins A1, A3 (=gibberellic acid), A4 and A7; gibberellic acid isespecially preferably used. The gibberellins are known (cf. R. Wegler“Chemie der Pflanzenschutz- and Schädlingsbekämpfungsmittel”, vol. 2,Springer Verlag, 1970, pp. 401-412).

The seed dressing formulations usable in accordance with the inventioncan be used to treat a wide variety of different kinds of seed eitherdirectly or after prior dilution with water. For instance, theconcentrates or the preparations obtainable therefrom by dilution withwater can be used to dress the seed of cereals, such as wheat, barley,rye, oats, and triticale, and also the seed of maize, rice, oilseedrape, peas, beans, cotton, sunflowers, soya beans and beets, or else awide variety of different vegetable seed. The seed dressing formulationsusable in accordance with the invention, or the dilute use formsthereof, can also be used to dress seed of transgenic plants.

For treatment of seed with the seed dressing formulations usable inaccordance with the invention, or the use forms prepared therefrom byadding water, all mixing units usable customarily for the seed dressingare useful. Specifically, the procedure in the seed dressing is to placethe seed into a mixer, operated batch-wise or continuously, to add theparticular desired amount of seed dressing formulations, either as suchor after prior dilution with water, and to mix everything until theformulation is distributed homogeneously on the seed. If appropriate,this is followed by a drying operation.

The application rate of the seed dressing formulations usable inaccordance with the invention can be varied within a relatively widerange. It is guided by the particular content of the compounds of theformula (I) in the formulations and by the seed. The application ratesof the compound of the formula (I) are generally between 0.001 and 50 gper kilogram of seed, preferably between 0.01 and 15 g per kilogram ofseed.

Animal Health

In the animal health field, i.e. in the field of veterinary medicine,the compounds of the formula (I) are active against animal parasites, inparticular ectoparasites or endoparasites. The term endoparasiteincludes in particular helminths and protozoae, such as coccidia.Ectoparasites are typically and preferably arthropods, in particularinsects or acarids.

In the field of veterinary medicine the compounds of the formula (I) aresuitable, with favourable toxicity in warm blooded animals, forcontrolling parasites which occur in animal breeding and animalhusbandry in livestock, breeding, zoo, laboratory, experimental anddomestic animals. They are active against all or specific stages ofdevelopment of the parasites.

Agricultural livestock include, for example, mammals, such as, sheep,goats, horses, donkeys, camels, buffaloes, rabbits, reindeers, fallowdeers, and in particular cattle and pigs; or poultry, such as turkeys,ducks, geese, and in particular chickens; or fish or crustaceans, e.g.in aquaculture; or, as the case may be, insects such as bees.

Domestic animals include, for example, mammals, such as hamsters, guineapigs, rats, mice, chinchillas, ferrets or in particular dogs, cats; cagebirds; reptiles; amphibians or aquarium fish.

According to a particular embodiment, the compounds of the formula (I)are administered to mammals.

According to another particular embodiment, the compounds of the formula(I) are administered to birds, namely cage birds or in particularpoultry.

By using the compounds of the formula (I) to control animal parasites,it is intended to reduce or prevent illness, cases of deaths andperformance reductions (in the case of meat, milk, wool, hides, eggs,honey and the like), so that more economical and simpler animal keepingis made possible and better animal well-being is achievable.

The term “control” or “controlling”, as used herein with regard to theanimal health field, means that the compounds of the formula (I) areeffective in reducing the incidence of the respective parasite in ananimal infected with such parasites to innocuous levels. Morespecifically, “controlling”, as used herein, means that the compounds ofthe formula (I) are effective in killing the respective parasite,inhibiting its growth, or inhibiting its proliferation.

Exemplary arthropods include, without any limitation

from the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.;from the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example Bovicola spp., Damalina spp., Felicola spp.,Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp.,Trinoton spp., Werneckiella spp.;from the order of the Diptera and the suborders Nematocerina andBrachycerina, for example Aedes spp., Anopheles spp., Atylotus spp.,Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culexspp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp.,Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp.,Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Luciliaspp., Lutzomyia spp., Melophagus spp., Morellia spp., Musca spp.,Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp.,Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanusspp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp.from the order of the Siphonapterida, for example Ceratophyllus spp.;Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp.;from the order of the Heteropterida, for example Cimex spp.,Panstrongylus spp., Rhodnius spp., Triatoma spp.; as well as nuisanceand hygiene pests from the order of the Blattarida.

Further, among the arthropods, the following acari may be mentioned byway of example, without any limitation:

from the subclass of the Acari (Acarina) and the order of theMetastigmata, for example, from the family of argasidae like Argas spp.,Ornithodorus spp., Otobius spp., from the family of Ixodidae likeAmblyomma spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp.,Ixodes spp., Rhipicephalus (Boophilus) spp. Rhipicephalus spp. (theoriginal genus of multi host ticks); from the order of mesostigmata likeDermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietiaspp., Sternostoma spp., Tropilaelaps spp., Varroa spp.; from the orderof the Actinedida (Prostigmata), for example Acarapis spp., Cheyletiellaspp., Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp.,Ornithocheyletia spp., Psorergates spp., Trombicula spp.; and from theorder of the Acaridida (Astigmata), for example Acarus spp., Caloglyphusspp., Chorioptes spp., Cytodites spp., Hypodectes spp., Knemidocoptesspp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptesspp., Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp.

Exemplary parasitic protozoa include, without any limitation:

Mastigophora (Flagellata) such as:

Metamonada: from the order Diplomonadida, for example, Giardia spp.,Spironucleus spp.

Parabasala: from the order Trichomonadida, for example, Histomonas spp.,Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp.,Tritrichomonas spp.

Euglenozoa: from the order Trypanosomatida, for example, Leishmaniaspp., Trypanosoma spp Sarcomastigophora (Rhizopoda), such asEntamoebidae, for example, Entamoeba spp., Centramoebidae, for example,Acanthamoeba sp., Euamoebidae, e.g. Hartmanella sp.

Alveolata such as Apicomplexa (Sporozoa): e.g. Cryptosporidium spp.;from the order Eimeriida, for example, Besnoitia spp., Cystoisosporaspp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp.,Sarcocystis spp., Toxoplasma spp.; from the order Adeleida e.g.Hepatozoon spp., Klossiella spp.; from the order Haemosporida e.g.Leucocytozoon spp., Plasmodium spp.; from the order Piroplasmida e.g.Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp.; from theorder Vesibuliferida e.g. Balantidium spp., Buxtonella spp.

Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidiumspp., Nosema spp., and furthermore, e.g. Myxozoa spp.

Helminths pathogenic for humans or animals include, for example,acanthocephala, nematodes, pentastoma and platyhelmintha (e.g.monogenea, cestodes and trematodes).

Exemplary helminths include, without any limitation:

Monogenea: e.g.: Dactylogyrus spp., Gyrodactylus spp., Microbothriumspp., Polystoma spp., Troglocephalus spp.

Cestodes: from the order of the Pseudophyllidea, for example: Bothridiumspp., Diphyllobothrium spp., Diplogonoporus spp., Ichthyobothrium spp.,Ligula spp., Schistocephalus spp., Spirometra spp. from the order of theCyclophyllida, for example: Andyra spp., Anoplocephala spp., Avitellinaspp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp.,Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotylespp., Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeuxiellaspp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp.,Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp.,Thysanosoma spp.

Trematodes: from the class of the Digenea, for example: Austrobilharziaspp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchisspp. Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoeliumspp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp.,Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp.,Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp.,Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeumspp., Leucochloridium spp., Metagonimus spp., Metorchis spp.,Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Ornithobilharziaspp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp.,Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp.,Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.

Nematodes: from the order of the Trichinellida, for example: Capillariaspp., Eucoleus spp., Paracapillaria spp., Trichinella spp.,Trichomosoides spp., Trichuris spp. from the order of the Tylenchida,for example: Micronema spp., Parastrongyloides spp., Strongyloides spp.

from the order of the Rhabditina, for example: Aelurostrongylus spp.,Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonemaspp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp.,Crenosoma spp., Cyathostomum spp., Cyclococercus spp., Cyclodontostomumspp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp.,Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroidesspp., Globocephalus spp., Graphidium spp., Gyalocephalus spp.,Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagiaspp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirusspp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp.,Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp.;Ornithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperiaspp., Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp.,Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp.,Protostrongylus spp., Spicocaulus spp., Stephanurus spp., Strongylusspp., Syngamus spp., Teladorsagia spp., Trichonema spp.,Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp.,Uncinaria spp.from the order of the Spirurida, for example: Acanthocheilonema spp.,Anisakis spp., Ascaridia spp.; Ascaris spp., Ascarops spp., Aspiculurisspp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp.,Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp.;Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp.,Gongylonema spp., Habronema spp., Heterakis spp.; Litomosoides spp., Loaspp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp.,Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp.,Pseudofilaria spp., Setaria spp., Skjrabinema spp., Spirocerca spp.,Stephanofilaria spp., Strongyluris spp., Syphacia spp., Thelazia spp.,Toxascaris spp., Toxocara spp., Wuchereria spp.

Acantocephala: from the order of the Oligacanthorhynchida, for example:Macracanthorhynchus spp., Prosthenorchis spp.; from the order of theMoniliformida, for example: Moniliformis spp.

from the order of the Polymorphida, for example: Filicollis spp.; fromthe order of the Echinorhynchida, for example: Acanthocephalus spp.,Echinorhynchus spp., Leptorhynchoides spp.

Pentastoma: from the order of the Porocephalida, for example: Linguatulaspp.

In the veterinary field and in animal keeping, the administration of thecompounds of the formula (I) is carried out by methods generally knownin the art, such as enterally, parenterally, dermally or nasally, in theform of suitable preparations. Administration can be carried outprophylactically, methaphylactically or therapeutically.

Thus, one embodiment of the present invention refers to the compounds ofthe formula (I) for use as a medicament.

Another aspect refers to the compounds of the formula (I) for use as anantiendoparasitical agent.

Another particular aspect refers to the compounds of the formula (I) foruse as a anthelmintic agent, more particular for use as a nematicidalagent, a platyhelminthicidal agent, an acanthocephalicidal agent, or apentastomicidal agent.

Another particular aspect refers to the compounds of the formula (I) foruse as an antiprotozoal agent.

Another aspect refers to the compounds of the formula (I) for use as anantiectoparasitical agent, in particular an arthropodicidal agent, moreparticular an insecticidal agent or acaricidal agent.

Further aspects of the invention are veterinary formulations, comprisingan effective amount of at least one compound of the formula (I) and atleast one of the following: pharmaceutically acceptable excipient (e.g.solid or liquid diluents), pharmaceutically acceptable auxiliary (e.g.surfactants), in particular a pharmaceutically acceptable excipientand/or pharmaceutically acceptable auxiliary which is normally used inveterinary formulations.

A related aspect of the invention is a method for preparing a veterinaryformulation as described herein, comprising the step of mixing at leastone compound of the formula (I) with pharmaceutically acceptableexcipients and/or auxiliaries, in particular with pharmaceuticallyacceptable excipients and/or auxiliaries which are normally used inveterinary formulations.

Another particular aspect of the invention are veterinary formulations,selected from the group of ectoparasiticidal and endoparasiticidalformulations, more particular selected from the group of anthelmintic,antiprotozoal, and arthropodicidal formulations, even more particularselected from the group of nematicidal, platyhelminthicidal,acanthocephalicidal, pentastomicidal, insecticidal, and acaricidalformulations, in accordance with the mentioned aspects, as well as theirmethods for preparation.

Another aspect refers to a method for treatment of a parasiticinfection, in particular an infection by a parasite selected from thegroup of ectoparasites and endoparasites mentioned herein, by applyingan effective amount of a compound of the formula (I) to an animal, inparticular a non-human animal, in need thereof.

Another aspect refers to a method for treatment of a parasiticinfection, in particular an infection by a parasite selected from thegroup of ectoparasites and endoparasites mentioned herein, by applying aveterinary formulation as defined herein to an animal, in particular anon-human animal, in need thereof.

Another aspect refers to the use of the compounds of the formula (I) inthe treatment of a parasitic infection, in particular an infection by aparasite selected from the group of ectoparasites and endoparasitesmentioned herein, in an animal, in particular a non-human animal.

In the present context of the animal health or veterinary field, theterm “treatment” includes prophylactic, metaphylactic or therapeuticaltreatment.

In a particular embodiment, mixtures of at least one compound of theformula (I) with other active ingredients, particularly with endo- andectoparasiticides, for the veterinary field are provided herewith.

In the field of animal health “mixture” not only means that two (ormore) different active ingredients are formulated in a joint formulationand are accordingly applied together but also refers to products whichcomprise separate formulations for each active compound. Accordingly, ifmore than two active compounds are to be applied, all active compoundsmay be formulated in a joint formulation or all active compounds may beformulated in separate formulations; also feasible are mixed forms wheresome of the active compounds are formulated jointly and some of theactive compounds are formulated separately. Separate formulations allowthe separate or successive application of the active compounds inquestion.

The active compounds specified herein by their common names are knownand described, for example, in the Pesticide Manual (see above) or canbe searched in the internet (e.g. http://www.alanwood.net/pesticides).

Exemplary active ingredients from the group of ectoparasiticides, asmixing partners, include, without limitation insecticides and acaricideslisted in detail above. Further active ingredients which may be used arelisted below following the aforementioned classification which is basedon the current IRAC Mode of Action Classification Scheme: (1)Acetylcholinesterase (AChE) inhibitors; (2) GABA-gated chloride channelblockers; (3) Sodium channel modulators; (4) Nicotinic acetylcholinereceptor (nAChR) competitive modulators; (5) Nicotinic acetylcholinereceptor (nAChR) allosteric modulators; (6) Glutamate-gated chloridechannel (GluCl) allosteric modulators; (7) Juvenile hormone mimics; (8)Miscellaneous non-specific (multi-site) inhibitors; (9) Modulators ofChordotonal Organs; (10) Mite growth inhibitors; (12) Inhibitors ofmitochondrial ATP synthase, such as, ATP disruptors; (13) Uncouplers ofoxidative phosphorylation via disruption of the proton gradient; (14)Nicotinic acetylcholine receptor channel blockers; (15) Inhibitors ofchitin biosynthesis, type 0; (16) Inhibitors of chitin biosynthesis,type 1; (17) Moulting disruptor (in particular for Diptera, i.e.dipterans); (18) Ecdysone receptor agonists; (19) Octopamine receptoragonists; (21) Mitochondrial complex I electron transport inhibitors;(25) Mitochondrial complex II electron transport inhibitors; (20)Mitochondrial complex III electron transport inhibitors; (22)Voltage-dependent sodium channel blockers; (23) Inhibitors of acetyl CoAcarboxylase; (28) Ryanodine receptor modulators;

Active compounds with unknown or non-specific mode of action, e.g.,fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform,flubenzimine, dicyclanil, amidoflumet, quinomethionate, triarathene,clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazone,gossyplure, flutenzin, bromopropylate, cryolite;

Compounds from other classes, e.g. butacarb, dimetilan, cloethocarb,phosphocarb, pirimiphos (-ethyl), parathion (-ethyl), methacrifos,isopropyl o-salicylate, trichlorfon, tigolaner, sulprofos, propaphos,sebufos, pyridathion, prothoate, dichlofenthion,demeton-S-methylsulphone, isazofos, cyanofenphos, dialifos,carbophenothion, autathiofos, aromfenvinfos (-methyl), azinphos(-ethyl), chlorpyrifos (-ethyl), fosmethilan, iodofenphos,dioxabenzofos, formothion, fonofos, flupyrazofos, fensulfothion,etrimfos; organochlorines, e.g. camphechlor, lindane, heptachlor; orphenylpyrazoles, e.g. acetoprole, pyrafluprole, pyriprole, vaniliprole,sisapronil; or isoxazolines, e.g. sarolaner, afoxolaner, lotilaner,fluralaner;

pyrethroids, e.g. (cis-, trans-), metofluthrin, profluthrin, flufenprox,flubrocythrinate, fubfenprox, fenfluthrin, protrifenbute, pyresmethrin,RU15525, terallethrin, cis-resmethrin, heptafluthrin, bioethanomethrin,biopermethrin, fenpyrithrin, cis-cypermethrin, cis-permethrin,clocythrin, cyhalothrin (lambda-), chlovaporthrin, or halogenatedcarbonhydrogen compounds (HCHs),neonicotinoids, e.g. nithiazinedicloromezotiaz, triflumezopyrimmacrocyclic lactones, e.g. nemadectin, ivermectin, latidectin,moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate;milbemycin oximetriprene, epofenonane, diofenolan;

Biologicals, hormones or pheromones, for example natural products, e.g.thuringiensin, codlemone or neem components

dinitrophenols, e.g. dinocap, dinobuton, binapacryl;benzoylureas, e.g. fluazuron, penfluron,amidine derivatives, e.g. chlormebuform, cymiazole, demiditraz

Bee hive varroa acaricides, for example organic acids, e.g. formic acid,oxalic acid.

Exemplary active ingredients from the group of endoparasiticides, asmixing partners, include, without limitation, anthelmintically activecompounds and antiprotozoal active compounds.

Anthelmintically active compounds, including, without limitation, thefollowing nematicidally, trematicidally and/or cestocidally activecompounds:

from the class of macrocyclic lactones, for example: eprinomectin,abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin,latidectin, milbemectin, ivermectin, emamectin, milbemycin;from the class of benzimidazoles and probenzimidazoles, for example:oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole,oxfendazole, netobimin, fenbendazole, febantel, thiabendazole,cyclobendazole, cambendazole, albendazole-sulphoxide, albendazole,flubendazole;from the class of depsipeptides, preferably cyclic depsipetides, inparticular 24-membered cyclic depsipeptides, for example: emodepside,PF1022A;from the class of tetrahydropyrimidines, for example: morantel,pyrantel, oxantel;from the class of imidazothiazoles, for example: butamisole, levamisole,tetramisole;from the class of aminophenylamidines, for example: amidantel,deacylated amidantel (dAMD), tribendimidine;from the class of aminoacetonitriles, for example: monepantel;from the class of paraherquamides, for example: paraherquamide,derquantel;from the class of salicylanilides, for example: tribromsalan,bromoxanide, brotianide, clioxanide, closantel, niclosamide,oxyclozanide, rafoxanide;from the class of substituted phenols, for example: nitroxynil,bithionol, disophenol, hexachlorophene, niclofolan, meniclopholan;from the class of organophosphates, for example: trichlorfon,naphthalofos, dichlorvos/DDVP, crufomate, coumaphos, haloxon;from the class of piperazinones/quinolines, for example: praziquantel,epsiprantel;from the class of piperazines, for example: piperazine, hydroxyzine;from the class of tetracyclines, for example: tetracyclin,chlorotetracycline, doxycyclin, oxytetracyclin, rolitetracyclin;from diverse other classes, for example: bunamidine, niridazole,resorantel, omphalotin, oltipraz, nitroscanate, nitroxynile,oxamniquine, mirasan, miracil, lucanthone, hycanthone, hetolin, emetine,diethylcarbamazine, dichlorophen, diamfenetide, clonazepam, bephenium,amoscanate, clorsulon.

Antiprotozoal active compounds, including, without limitation, thefollowing active compounds:

from the class of triazines, for example: diclazuril, ponazuril,letrazuril, toltrazuril;from the class of polylether ionophore, for example: monensin,salinomycin, maduramicin, narasin;from the class of macrocyclic lactones, for example: milbemycin,erythromycin;from the class of quinolones, for example: enrofloxacin, pradofloxacin;from the class of quinines, for example: chloroquine;from the class of pyrimidines, for example: pyrimethamine;from the class of sulfonamides, for example: sulfaquinoxaline,trimethoprim, sulfaclozin;from the class of thiamines, for example: amprolium;from the class of lincosamides, for example: clindamycin;from the class of carbanilides, for example: imidocarb;from the class of nitrofuranes, for example: nifurtimox;from the class of quinazolinone alkaloids, for example: halofuginon;from diverse other classes, for example: oxamniquin, paromomycin;from the class of vaccines or antigenes from microorganisms, forexample: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimerianecatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeriaacervulina, Babesia canis vogeli, Leishmania infantum, Babesia caniscanis, Dictyocaulus viviparus.

All named mixing partners can, if their functional groups enable this,optionally form salts with suitable bases or acids.

Vector Control

The compounds of the formula (I) can also be used in vector control. Forthe purpose of the present invention, a vector is an arthropod, inparticular an insect or arachnid, capable of transmitting pathogens suchas, for example, viruses, worms, single-cell organisms and bacteria froma reservoir (plant, animal, human, etc.) to a host. The pathogens can betransmitted either mechanically (for example trachoma by non-stingingflies) to a host, or by injection (for example malaria parasites bymosquitoes) into a host.

Examples of vectors and the diseases or pathogens they transmit are:

1) Mosquitoes

-   -   Anopheles: malaria, filariasis;    -   Culex: Japanese encephalitis, other viral diseases, filariasis,        transmission of other worms;    -   Aedes: yellow fever, dengue fever, other viral diseases,        filariasis;    -   Simuliidae: transmission of worms, in particular Onchocerca        volvulus;    -   Psychodidae: transmission of leishmaniasis        2) Lice: skin infections, epidemic typhus;        3) Fleas: plague, endemic typhus, cestodes;        4) Flies: sleeping sickness (trypanosomiasis); cholera, other        bacterial diseases;        5) Mites: acariosis, epidemic typhus, rickettsialpox,        tularaemia, Saint Louis encephalitis, tick-borne encephalitis        (TBE), Crimean-Congo haemorrhagic fever, borreliosis;        6) Ticks: borellioses such as Borrelia burgdorferi sensu lato.,        Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella        burnetii), babesioses (Babesia canis canis), ehrlichiosis.

Examples of vectors in the sense of the present invention are insects,for example aphids, flies, leafhoppers or thrips, which are capable oftransmitting plant viruses to plants. Other vectors capable oftransmitting plant viruses are spider mites, lice, beetles andnematodes.

Further examples of vectors in the sense of the present invention areinsects and arachnids such as mosquitoes, in particular of the generaAedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A.dirus (malaria) and Culex, psychodids such as Phlebotomus, Lutzomyia,lice, fleas, flies, mites and ticks capable of transmitting pathogens toanimals and/or humans.

Vector control is also possible if the compounds of the formula (I) areresistance-breaking.

Compounds of the formula (I) are suitable for use in the prevention ofdiseases and/or pathogens transmitted by vectors. Thus, a further aspectof the present invention is the use of compounds of the formula (I) forvector control, for example in agriculture, in horticulture, in gardensand in leisure facilities, and also in the protection of materials andstored products.

Protection of Industrial Materials

The compounds of the formula (I) are suitable for protecting industrialmaterials against attack or destruction by insects, for example from theorders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera andZygentoma.

Industrial materials in the present context are understood to meaninanimate materials, such as preferably plastics, adhesives, sizes,papers and cards, leather, wood, processed wood products and coatingcompositions. The use of the invention for protecting wood isparticularly preferred.

In a further embodiment, the compounds of the formula (I) are usedtogether with at least one further insecticide and/or at least onefungicide.

In a further embodiment, the compounds of the formula (I) are present asa ready-to-use pesticide, i.e. they can be applied to the material inquestion without further modifications. Suitable further insecticides orfungicides are in particular those mentioned above.

Surprisingly, it has also been found that the compounds of the formula(I) can be employed for protecting objects which come into contact withsaltwater or brackish water, in particular hulls, screens, nets,buildings, moorings and signalling systems, against fouling. Likewise,the compounds of the formula (I), alone or in combinations with otheractive compounds, can be used as antifouling agents.

Control of Animal Pests in the Hygiene Sector

The compounds of the formula (I) are suitable for controlling animalpests in the hygiene sector. In particular, the invention can be appliedin the domestic sector, in the hygiene sector and in the protection ofstored products, especially for controlling insects, arachnids, ticksand mites encountered in enclosed spaces such as dwellings, factoryhalls, offices, vehicle cabins, animal husbandries. For controllinganimal pests, the compounds of the formula (are used alone or incombination with other active compounds and/or auxiliaries. They arepreferably used in domestic insecticide products. The compounds of theformula (I) are effective against sensitive and resistant species, andagainst all developmental stages.

These pests include, for example, pests from the class Arachnida, fromthe orders Scorpiones, Araneae and Opiliones, from the classes Chilopodaand Diplopoda, from the class Insecta the order Blattodea, from theorders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera,Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria orOrthoptera, Siphonaptera and Zygentoma and from the class Malacostracathe order Isopoda.

They are used, for example, in aerosols, pressure-free spray products,for example pump and atomizer sprays, automatic fogging systems,foggers, foams, gels, evaporator products with evaporator tablets madeof cellulose or plastic, liquid evaporators, gel and membraneevaporators, propeller-driven evaporators, energy-free, or passive,evaporation systems, moth papers, moth bags and moth gels, as granulesor dusts, in baits for spreading or in bait stations.

Abbreviations and Symbols

-   AcOH: acetic acid-   aq.: aqueous-   br.: broad-   d: doublet-   DCC: N,N′-dicyclohexylcarbodiimide-   DIPEA: N,N-diisopropylethylamine-   DMF: N,N-dimethylformamide-   DMSO: dimethylsulfoxide-   ee: enantiomeric excess-   eq.: equivalent-   ES: electrospray ionization-   Et₃N triethylamine-   EtOAc: ethyl acetate-   hr(s) hour(s)-   HATU:    1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxid    hexafluorophosphate-   HOBt: 1-hydroxybenzotriazole hydrate-   HPLC: high performance liquid chromatography-   iPrOH: isopropanol-   J: coupling constant-   LCMS: liquid chromatography-mass spectrometry-   m/z: mass-to-charge ratio-   M: molarity-   m: multiplet-   MeCN acetonitrile-   MeOH: methanol-   NaH₂PO₄ monosodium phosphate-   NaOH sodium hydroxide-   Na₂SO₄ sodium sulfate-   NH₄Cl ammonium chloride-   NMR: nuclear magnetic resonance-   q: quartet-   r. t.: room temperature-   R_(t): retention time-   s: singlet-   sat.: saturated-   T: temperature-   t: triplet-   T3P®: propylphosphonic anhydride-   THF: tetrahydrofuran-   TMSOK potassium trimethylsilanolate-   wt.: weight-   δ: chemical shift-   λ: wavelength

Description of the Processes and Intermediates

Compounds of formula I′ may be prepared as illustrated in the followingscheme 1 where R¹, R², R^(3a), R^(3b), R⁴, Q¹, Q² and Y are aspreviously defined and X stands for OH or Cl.

X=OH: An azole compound of formula (a) is reacted with a carboxylic acidof formula (b) (X=OH) to form compounds of formula I′. For example, amixture of an azole of formula (a), a carboxylic acid of formula (b)(X=OH), a suitable coupling reagent, such as T3P®, HATU, DCC or HOBt, asuitable base such as triethylamine or DIPEA, in a suitable solvent,such as ethyl acetate or DMF are mixed at temperatures ranging fromaround 0 to 100° C. to provide compounds of formula I′ which may then beisolated and, if necessary and desired, purified using techniques wellknown in the art, such as chromatography.

X=Cl: An azole compound of formula (a) is reacted with a carboxylic acidchloride of formula (b) (X=Cl) to form compounds of formula I′. Forexample, a mixture of an azole of formula (a), a carboxylic acidchloride of formula (b) (X=Cl), a suitable base such as triethylamine orDIPEA, in a suitable solvent, such as dichloromethane or THF are mixedat temperatures ranging from around 0 to 100° C. to provide compounds offormula I′ which may then be isolated and, if necessary and desired,purified using techniques well known in the art, such as chromatography.

Carboxylic acids of formula (b) (X=OH) and carboxylic acid chlorides offormula (b) (X=Cl) are commercially available or may be synthesized bymethods known to a person skilled in the state of the art.

For example, the carboxylic acids employed for the synthesis of examplesI-048 and I-049 can be synthesized in analogy to WO 2016198507, WO2015084936, WO 2015148354, WO 2015148373 using a similar catalyticsystem as described in the referenced, consisting of copper(I)iodide and(E,E)-N,N′-cyclohexane-1,2-diylbis[1-(pyridin-2-yl)methanimine], for thelatter see US 20030236413.

The requisite azole compounds of formula (a) may be prepared asillustrated in the following scheme 2, where R¹, R^(3a), R^(3b), R⁴, Q¹,Q² and Y are as previously described and LG is a suitable leaving group(see also WO 2017192385).

An amine of formula (c) is reacted with a substituted azole of formula(d) to form compounds of formula (a). For example, a mixture of an azoleof formula (d), an amine of formula (c), a suitable base, such as K₂CO₃,NaH or DIPEA in a suitable solvent, such as acetonitrile or DMF aremixed at temperatures ranging from around 20 to 120° C. to providecompounds of formula (a) which may then be isolated and, if necessaryand desired, purified using techniques well known in the art, such aschromatography.

Alternatively, a substituted azole of formula (d) is reacted withammonia to form compounds of formula (e). For example, a solution ofammonia in a suitable solvent, such as methanol, and a substituted azoleof formula (d) are mixed in a sealed tube at temperatures ranging fromaround 0 to 25° C. to provide compounds of formula (e) which may then beisolated and, if necessary and desired, purified using techniques wellknown in the art, such as trituration. A substituted azole of formula(e), a compound of formula (f), a suitable base, such as K₂CO₃ or DIPEAin a suitable solvent, such as acetonitrile or DMF are mixed attemperatures ranging from around 20 to 120° C. to provide compounds offormula (a) which may then be isolated and, if necessary and desired,purified using techniques well known in the art such as chromatography.

Amines of formula (c) and compounds of formula (f) are commerciallyavailable or may be synthesized by methods known to a person skilled inthe state of the art. The requisite azole compounds of formula (d) maybe prepared as illustrated in the following scheme 3, where R^(3a),R^(3b), R⁴, R⁵, Q¹, Q² and Y are as previously described, LG is asuitable leaving group (see also WO 2017192385).

An amide of formula (h) is reacted with an N,N-dimethylamide dimethylacetal (g) to form compounds of formula (i) which are subsequentlyreacted with hydrazines (j) under acidic conditions to form compounds offormula (d). For example, a compound of formula (h) and anN,N-dimethylamide dimethyl acetal of formula (g) are reacted in asuitable solvent, such as CH₂Cl₂ at reflux to provide compounds offormula (i). Upon removal of the solvent, compounds of formula (i) arereacted with a substituted hydrazine (j) in a suitable solvent such as1,4-dioxane, acetic acid or a mixture of such solvents at temperaturesranging from around 20 to 100° C. to provide compounds of formula (d)which may then be isolated and, if necessary and desired, purified usingtechniques well known in the art, such as chromatography.

Alternatively, a carboxylic acid derivative of formula (k) is reactedwith an amine of formula (I) and a suitable base, such as triethylamineor DIPEA, in a suitable solvent, such as toluene, at temperaturesranging from around 0 to 120° C. The resulting compounds (m) may then beisolated and, if necessary and desired, purified using techniques wellknown in the art, such as chromatography. The resulting amides offormula (m) and phosphorus pentachloride are reacted in a suitablesolvent, such as CH₂Cl₂, at r.t. and then trimethylsilyl azide is addedto the mixture at 0° C. and the mixture is stirred at r.t. to providecompounds of formula (d) which may then be isolated and, if necessaryand desired, purified using techniques well known in the art, such aschromatography.

N,N-dimethylamide acetals of formula (g), amides of formula (h),carboxylic acid derivatives of formula (k) and hydrazines of formula U)are commercially available or may be synthesized by methods known to aperson skilled in the state of the art.

Compounds of formula I″a may be prepared as illustrated in the followingscheme 4 where R¹, R², R^(3a), R^(3b), R⁴, R⁵ and Y are as previouslydefined.

An amide of formula (n) is reacted with an N,N-dimethylamide dimethylacetal of formula (g) to form compounds of formula (o) which aresubsequently reacted with substituted hydrazines of formula U) underacidic conditions to form compounds of formula I″a. For example, acompound of formula (n) and an N,N-dimethylamide dimethyl acetal offormula (g) are reacted in a suitable solvent, such as CH₂Cl₁₂ at refluxto provide compounds of formula (o). Upon removal of the solvent,compounds of formula (o) are reacted with a substituted hydrazine offormula (i) in a suitable solvent such as 1,4-dioxane, acetic acid or amixture of such solvents at temperatures ranging from around 20 to 100°C. The resulting compounds of formula I″a may then be isolated and, ifnecessary and desired, purified using techniques well known in the art,such as chromatography.

The requisite amides of formula (n) may be prepared as illustrated inthe following scheme 5, where R¹, R², R³, and Y are as previouslydescribed (see also WO 2017192385).

An amino amide of formula (p) is reacted with a carboxylic acid offormula (b) to form compounds of formula (n). For example, a mixture ofan amino amide of formula (p), a carboxylic acid (b), a suitablecoupling reagent, such as T3P®, HATU, DCC or HOBt, a suitable base suchas triethylamine or DIPEA, in a suitable solvent such as ethyl acetateor DMF are mixed at temperatures ranging from around 0 to 100° C. toprovide compounds of formula (n) which may then be isolated and, ifnecessary and desired, purified using techniques well known in the art,such as chromatography.

Alternatively, an amino acid of formula (q) is reacted with thionylchloride in a suitable solvent, such as MeOH, at r.t. to provide aminoesters of formula (r). The resulting amino esters (r) are reacted withan aldehyde or a ketone, a suitable reducing agent such as sodiumtriacetoxyborohydride, a dehydrating agent such as Na₂SO₄, in a suitablesolvent such as acetic acid, at r.t. to provide compounds of formula(s). The resulting amino esters of formula (s) are then reacted with acarboxylic acid of formula (b), a suitable coupling reagent, such asT3P, a suitable base such as DIPEA, in a suitable solvent, such as ethylacetate at about 90° C. to provide amido esters of formula (t) which maythen be isolated and, if necessary and desired, purified usingtechniques well known in the art, such as chromatography. The resultingamido esters of formula (t) are reacted with magnesium nitride in asuitable solvent, such as MeOH at about 80° C. in a sealed tube toprovide compounds of formula (n) which may then be isolated and, ifnecessary and desired, purified using techniques well known in the art,such as chromatography or extraction.

Compounds of formula (b) and (q) are commercially available. Therequisite amino amide compounds of formula (p) are commerciallyavailable or may be prepared as illustrated in the following scheme 6,where R¹, R^(3a), R^(3b), and Y are as previously described and LG is asuitable leaving group (see also WO 2017192385).

Compounds of formula (c) and (h) are commercially available.

An amine of formula (c) is reacted with an amide of formula (h) to formcompounds of formula (p). For example, a mixture of an amine of formula(c), an amide of formula (h), a suitable base, such as K₂CO₃ or DIPEA ina suitable solvent, such as acetonitrile or DMF are mixed at 25-80° C.to provide compounds of formula (p) which may then be isolated and, ifnecessary and desired, purified using techniques well known in the art,such as chromatography.

In an alternative approach compounds of formula I″a may be prepared asillustrated in the following scheme 7 where R¹. R², R^(3a), R^(3b), R⁴,R⁵ and Y are as previously defined.

An amidine hydrochloride of formula (u) is reacted with an acid offormula (v). For example, an amidine hydrochloride of formula (u), acarboxylic acid (v), a suitable coupling reagent, such as HATU, DCC orHOBt, a suitable base such as triethylamine or DIPEA, in a suitablesolvent such as acetonitrile or DMF are mixed at temperatures rangingfrom around 0 to 100° C., to form compounds of formula (w) which aresubsequently reacted with substituted hydrazines of formula (j) underacidic conditions to form compounds of formula I″a which may then beisolated and, if necessary and desired, purified using techniques wellknown in the art, such as chromatography.

Amidine hydrochlorides of formula (u), carboxylic acid derivatives offormula (v) and hydrazines of formula (j) are commercially available ormay be synthesized by methods known to the skilled artisan.

Sulfoxides (sulfines) of the general formula (ya) and sulfones of theformula (yb) may be prepared as illustrated in the following scheme 8wherein Ar is phenyl or hetaryl and R^(X) is C₁-C₆alkyl, C₁-C₆haloalkyl,optionally substituted phenyl or optionally substituted C₃-C₆cycloalkyl

A sulfanyl group containing compound of formula (x) is reacted with anoxidizing reagent such as 3-chloroperoxybenzoic acid or ruthenium(III)chloride in combination with sodium periodate to form compounds offormula (ya) or (yb), depending on the mol equivalent of the oxidizingreagent. Sulfinyl compounds of the formula (ya) are understood to formoptical isomers or isomer mixtures of varying composition. A sulfinylgroup containing compound of formula (ya) is reacted with an oxidizingreagent such as 3-chloroperoxybenzoic acid or ruthenium(III) chloride incombination with sodium periodate to form sulfone containing compoundsof formula (yb).

Compounds of formula (zb) may be prepared as illustrated in thefollowing scheme 9 wherein E is H or C₁-C₆alkyl, Hal is bromine oriodine, G is an optionally substituted phenyl or cyclopropyl, and A* ischlorine, fluorine, trifluoromethyl or trifluoromethoxy.

A halogen containing compound of formula (z) is reacted with a boronicacid of formula (za) to form compounds of formula (zb). For example, amixture of a halogen containing compound of formula (z), a boronic acid(za), a suitable catalyst, such as[1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) orpalladium(II) acetate in combination with tricyclohexylphosphine, asuitable base such as cesium carbonate, tripotassium phosphate or sodiumhydrogencarbonate, in a suitable solvent or solvent mixture suchas/containing 1,4-dioxane, ethanol, toluene or water are reacted attemperatures ranging from around 0 to 100° C. to provide compounds offormula (zb) which may then be isolated and, if necessary and desired,purified using techniques well known in the art, such as chromatography.Compounds of formula (zb) in which E is C₁-C₆alkyl can be transformed tocompounds of formula (zb) in which E is H by treatment with a an alkalihydroxide in a suitable solvent or solvent mixture such as/containingtetrahydrofuran, ethanol or water at temperatures ranging from around 0to 100° C.

Compounds of formula (zf) may be prepared as illustrated in thefollowing scheme 10 wherein Alk is C₁-C₆alkyl and A is chlorine,fluorine or cyano.

Boronic acids of formula (zc) may be prepared from the known boronicacid pinacol esters (WO 2011/023677, WO 2009/107391, WO 2010/069504) byhydrolysis using NaIO₄ (Journal of Organic Chemistry, 79(1), 328-338,2014).

A boronic acid of formula (zc) is reacted to trifluoromethylsulfanylcompounds of formula (zd) which are subsequently reacted with alkalihydroxides to form acids of formula (ze). The trifluoromethylsulfanylgroup in compounds of formula (ze) is then oxidized to givetrifluoromethylsulfonyl functionalized compounds of formula (zf).

For example, a mixture of a boronic acid of formula (zc),trimethyl(trifluoromethyl)silane, silver carbonate, tripotassiumphosphate, copper thiocyanate, 1,10-phenanthroline, sulfur and 4 Amolecular sieves, in a suitable solvent such as dimethylformamide arereacted at temperatures ranging from around 0 to 60° C. to providecompounds of formula (zd) which may then be isolated and, if necessaryand desired, purified using techniques well known in the art, such aschromatography (Angew. Chem. Int. Ed. 2012, 51, 2492-2495). Esters offormula (zd) and alkali hydroxides in a suitable solvent mixturecontaining for example water and tetrahydrofurane are reacted attemperatures ranging from around 0 to 100° C. to provide acids offormula (ze) which may then be isolated and, if necessary and desired,purified using techniques well known in the art, such as chromatography.Trifluoromethylsulfanyl compounds of formula (ze), ruthenium(III)chloride and sodium periodate, in a suitable solvent mixture containingfor example dichloromethane, acetonitrile and water are reacted attemperatures ranging from 0 to 60° C. to trifluoromethylsulfonylcompounds of formula (zf) which may then be isolated and, if necessaryand desired, purified using techniques well known in the art, such aschromatography.

Compounds of formula (zj) may be prepared as illustrated in thefollowing scheme 11 where R¹, R^(3a), R^(3b), R⁴, R⁵ and Y are aspreviously defined.

An amide of formula (zg) is reacted with an N,N-dimethylamide dimethylacetal of formula (g) to form compounds of formula (zh) which aresubsequently reacted with substituted hydrazines of formula U) underacidic conditions to form compounds of formula (zi). For example, acompound of formula (zg) and a N,N-dimethylamide dimethyl acetal offormula (g) are reacted in a suitable solvent, such as CH₂Cl₂ at refluxto provide compounds of formula (zh). After removal of the solvent,compounds of formula (zh) are reacted with a substituted hydrazine offormula) in a suitable solvent such as 1,4-dioxane, acetic acid or amixture of such solvents at temperatures ranging from around 20 to 80°C. The resulting compounds of formula (zi) may then be isolated and, ifnecessary and desired, purified using techniques well known in the art,such as chromatography.

A carbamate of formula (zi) is treated with an acid to form amines offormula (zj). For example, a carbamate of formula (zi) and a suitableacid, such as hydrogen chloride or trifluoracetic acid, are reacted in asuitable solvent, such as dioxane or in the case of trifluoroacetic acidwithout an additional solvent at temperatures ranging from around 0 to80° C. The resulting amines of formula (zj) may then be isolated astheir acid salts of after base treatment as free amines and, ifnecessary and desired, purified using techniques well known in the art,such as chromatography.

The requisite amides of formula (zg) and hydrazines of formula U) arecommercially available or may be synthesized by methods described inthis application or methods known to the skilled artisan.

Compounds of formula (zm) may be prepared as illustrated in thefollowing scheme 12 wherein Alk is C₁-C₆alkyl, Hal is iodine or bromine,Ra is C₁-C₆alkyl, cylopropyl or optionally substituted phenyl; and Rb ishalogen, C₁-C₆alkyl or C₃-C₆cycloalkyl. The phenyl ring may besubstituted by up to two Rb substitutents.

An aryl halide of formula (zk) is reacted with a sulfinate salt offormula (zl) under copper catalysis to form sulfones of formula (zm).For example, a mixture of a compound of formula (zk), a sodium sulfinatesalt of formula (zl), copper(I) iodide, proline and sodium hydroxide arereacted in a suitable solvent, such as dimethyl sulfoxide attemperatures ranging from 40 to 140° C. The resulting compounds offormula (zm) may then be isolated and, if necessary and desired,purified using techniques well known in the art, such as chromatography.Esters of formula (zm) can be hydrolyzed to the carboxylic acids bytreatment with a an alkali hydroxide in a suitable solvent or solventmixture such as/containing tetrahydrofuran, ethanol or water attemperatures ranging from around 0 to 100° C.

The requisite aryl halides (zk) and sulfonate salts of formula (zl) arecommercially available or may be synthesized by methods known to theskilled artisan.

Compounds of formula (zq) may be prepared as illustrated in thefollowing scheme 13, Hal is fluorine or chlorine, Rd is optionallysubstituted C₁-C₆alkyl or optionally substituted C₃-C₆cycloalkyl; and Reis halogen or in each case optionally substituted C₁-C₆alkyl,C₃-C₆cycloalkyl or C₁-C₄alkoxy. The phenyl ring may be substituted by upto two Rc substitutents.

An aryl halide of formula (zn) is reacted with a thiolate salt offormula (zo) to form thioethers of formula (zp) which are thenhydrolised to form carboxylic acids of formula (zq). For example, amixture of a halide of formula (zn) and a sodium thiolate of formula(zo), is reacted in a suitable solvent, such as N,N-dimethylformamide attemperatures ranging from −20 to 50° C. The resulting nitriles offormula (zp) are then hydrolized either under basic conditions, usingfor example aqueous sodium hydroxide in a suitable solvent, such asethanol at temperatures ranging from 40 to 100° C. or under acidicconditions in a suitable strong acid, such as sulfuric acid orhydrochloric acid either neat or diluted with a suitable dilutant suchas water at temperatures ranging from 40 to 100° C. The obtainedcarboxylic acids (zq) are then if necessary and desired, purified usingtechniques well known in the art, such as chromatography.

The requisite aryl halides (zn) and thiolate salts of formula (zo) arecommercially available or may be synthesized by methods known to theskilled artisan.

Compounds of formula I″b may be prepared as illustrated in the followingscheme 14 where R¹, R², R^(3a), R^(3b), R⁵ and Y are as previouslydefined. Bn is benzyl and LG is chloride or trifluoromethylsulfonyl.

A benzyl protected compound of formula (I″b) is deprotected to form analcohol of formula (I″c) which is then alkylated with an alkylatingagent of formula (zr) to form ethers of formula (I″d). For example, abenzyl protected compound of formula (I″b), is deprotected in thepresence of a suitable catalyst, such as palladium on charcoal under ahydrogen atmosphere, in a suitable solvent, such as methanol attemperatures ranging from −20 to 50° C. The resulting alcohols offormula (I″b) are then alkylated with a suitable alkylating agent suchas chloro(difluoro)methane (WO2016155884) or difluoromethyltrifluoromethanesulfonate (WO2016046166) in the presence of a suitablebase, such as potassium carbonate or potassium hydroxide in a suitablesolvent, such as acetonitrile or N,N-dimethylformamide at temperaturesranging from −30 to 50° C. The obtained ethers of formula (I″d) are thenif necessary and desired, purified using techniques well known in theart, such as chromatography.

The requisite benzyl protected compound of formula (I″b) may be preparedas described in Scheme 4 using hydrazines that may be synthesized bymethods known to the skilled artisan (e.g. as described in J. Am. Chem.Soc. 2017, 139, 42, 14833-14836).

Scheme 15 illustrates the preparation of 3-haloalkyl triazoles as showne.g. in example I-091. In a first step, a hydrazine amide is formed asdescribed in EP 1099695. In a second step,(αS)-1,3-dihydro-α-methyl-1,3-dioxo-2H-isoindole-2-acetyl chloride,prepared from (αS)-1,3-dihydro-α-methyl-1,3-dioxo-2H-isoindole-2-aceticacid (Pht-Ala-OH purchased from ABCR) and oxalyl chloride according toTetrahedron: Asymmetry, 21(8), 936-942, 2010, reacts with a hydrazoneamide in the presence of a base, like pyridine, as described in EP1099695. In a third step, the phthalimide protection group is removed byreaction with hydrazine hydrate in a suitable solvent, like ethanol, asdescribed in WO 2018086605. In a final step, the obtained amine isreacted with a carboxylic acid to form the example compound, e.g. 1-091.For example, a mixture of an amine, a carboxylic acid, a suitablecoupling reagent, such as T3P®,[O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium-hexafluorophosphate](HATU), dicyclohexylcarbodiimid (DCC),1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) orhydroxybenzotriazole (HOBt), a suitable base such as triethylamine orN,N-diisopropylethylamine, in a suitable solvent such as ethyl acetateor N,N-dimethylformamide are mixed at temperatures ranging from around 0to 100° C. to provide the example compound which may then be isolatedand, if necessary and desired, purified using techniques well known inthe art, such as chromatography.

Compounds of formula I″g and I″h may be prepared as illustrated in thefollowing scheme 16, where R¹, R², R^(3a), R^(3b), R and Y are aspreviously defined, T is R⁴ as previously described and at leastsubstituted with one —NO₂-group, LG is a suitable leaving group and Arepresents optionally substituted C₁-C₆alkyl, CO—C₁-C₆alkyl,CO—C₃-C₆cycloalkyl, CO-phenyl, or SO₂C₁-C₆alkyl.

A nitro compound of formula (I″e) is converted into the respective aminocompound of formula (I″f) under reducing conditions, likewise withhydrogen and palladium on charcoal in a suitable solvent like THF orethanol (European Journal of Medicinal Chemistry, 158, 322-333; 2018),with tin(II) chloride and HCl in a suitable solvent like ethanol (WO2018085247), with iron powder and HCl in a suitable solvent like ethanol(WO 2017216293) or with iron powder in a mixture of acetic acid andethanol The resulting amino compound (I″f) reacts, in the presence of asuitbale base such as DIPEA or potassium carbonate, with acylation,benzoylation, sulfonlyation or alkylation reagents A-LG of formula (zs).If one equivalent of A-LG is used compounds of formula (I″g) areobtained. Two equivalents of A-LG yield compounds of formula (I″h). Theobtained compounds of formula (I″h) and (I″g) are then if necessary anddesired, purified using techniques well known in the art, such aschromatography.

Compounds of formula I″k may be prepared as illustrated in the followingscheme 17, where R¹, R², R^(3a), R^(3b), R⁵ and Y are as previouslydefined, wherein T is R⁴ as previously described and at leastsubstituted with one —CO₂alkyl-group, —COOH or CON(E¹)E² grouprespectively. E¹ and E² are independently selected from the group of Hand in each case optionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl,phenyl or SO₂C₁-C₆alkyl.

An ester compound of formula (I″i) is saponified to obtain therespective carboxylic acid compound of formula (I″j) followed by anamide coupling step with amines of formula (zt) to obtain amides offormula (I″k) by methods known to a person skilled in the state of theart.

For example, a mixture of an amine of formula (zt), a carboxylic acid(I″j), a suitable coupling reagent, such as T3P®, HATU, DCC or HOBt, asuitable base such as triethylamine or DIPEA, in a suitable solvent suchas ethyl acetate or DMF are mixed at temperatures ranging from around 0to 100° C. to provide compounds of formula (I″k) which may then beisolated and, if necessary and desired, purified using techniques wellknown in the art, such as chromatography.

The preparation and use examples which follow illustrate the inventionwithout limiting it.

Preparation Examples Synthesis of3-chloro-N-(cyclopropylmethyl)-5-(methylsulfonyl)-N-{1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamide(example I-003)

A solution of 120 mg (491μmol)N-(cyclopropylmethyl)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethanamineand 127 mg (541 μmol) 3-chloro-5-(methylsulfonyl)benzoic acid in 5 mLethyl acetate was treated with 0.30 mL (1.7 mmol)N,N-Diisopropylethylamine and stirred for 10 min at room temperature.0.60 mL (0.84 mmol) of T3P® solution (50 wt. % in EtOAc) were added andthe reaction mixture was stirred at room temperature over night. Waterwas added, the layers separated and the aqueous layer was extractedseveral times with ethyl acetate. The combined organic layers weresequentially washed with water, aq. sat. NaHCO₃ and aq. sat. NH₄Cl. Thesolution was dried with Na₂SO₄, filtered and concentrated under reducedpressure. The residue was purified by HPLC (H₂O/acetonitrile) to provide125 mg of3-chloro-N-(cyclopropylmethyl)-5-(methylsulfonyl)-N-{1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamide.

¹H-NMR (600.1 MHz, CD₃CN, 260 K): NMR peaklist: δ=8.8859 (4.9); 8.8778(5.0); 8.6382 (1.6); 8.6302 (1.6); 8.0865 (4.4); 8.0335 (1.4); 8.0142(0.1); 7.9580 (2.7); 7.9433 (0.1); 7.9060 (0.1); 7.8124 (1.0); 7.7920(0.1); 7.6327 (1.0); 7.5286 (1.4); 7.5206 (2.6); 7.5125 (1.4); 7.4498(3.6); 7.4167 (0.5); 7.4088 (0.9); 7.4007 (0.5); 7.3889 (2.9); 6.3593(0.4); 6.3477 (1.4); 6.3361 (1.5); 6.3246 (0.5); 6.0860 (0.2); 6.0749(0.5); 6.0634 (0.5); 6.0517 (0.2); 3.8379 (0.3); 3.6910 (0.3); 3.6808(0.3); 3.6675 (0.4); 3.6571 (0.4); 3.5278 (0.4); 3.5160 (0.4); 3.5040(0.3); 3.4922 (0.3); 3.1910 (0.1); 3.1259 (0.4); 3.1151 (0.3); 3.0769(16.0); 3.0244 (0.2); 2.9592 (0.1); 2.9111 (0.6); 2.9037 (0.4); 2.8995(0.6); 2.8849 (1.3); 2.8733 (1.4); 2.8440 (1.3); 2.8345 (1.3); 2.8178(0.6); 2.8083 (0.6); 2.3015 (0.1); 2.2910 (81.9); 2.2744 (0.2); 2.2645(0.1); 2.2585 (0.1); 2.0800 (0.2); 2.0759 (0.4); 2.0718 (0.6); 2.0677(0.4); 2.0636 (0.2); 1.9851 (1.2); 1.9770 (1.0); 1.9726 (1.7); 1.9692(37.9); 1.9651 (74.7); 1.9609 (110.4); 1.9568 (76.7); 1.9527 (39.4);1.9440 (0.9); 1.9348 (0.4); 1.9307 (0.3); 1.9268 (0.2); 1.9226 (0.2);1.9182 (0.2); 1.9138 (0.2); 1.9096 (0.1); 1.8950 (0.1); 1.8916 (0.1);1.8873 (0.1); 1.8831 (0.1); 1.8789 (0.1); 1.8748 (0.1); 1.8707 (0.1);1.8622 (0.1); 1.8541 (0.3); 1.8500 (0.5); 1.8458 (0.7); 1.8417 (0.5);1.8376 (0.3); 1.8232 (6.0); 1.8116 (6.1); 1.7615 (2.1); 1.7501 (2.1);1.7134 (0.1); 1.7019 (0.1); 1.5085 (0.1); 1.3213 (0.2); 1.3132 (0.2);1.3096 (0.2); 1.3006 (0.2); 1.2879 (0.2); 1.2766 (0.2); 1.2716 (0.2);1.0585 (0.2); 1.0481 (0.3); 1.0378 (0.2); 0.8970 (0.2); 0.8858 (0.5);0.8738 (0.2); 0.5974 (0.1); 0.5877 (0.2); 0.5837 (0.2); 0.5752 (0.5);0.5643 (0.7); 0.5544 (0.6); 0.5418 (0.3); 0.5325 (0.1); 0.5107 (0.1);0.4954 (0.4); 0.4817 (0.6); 0.4741 (0.6); 0.4681 (0.6); 0.4602 (0.4);0.4523 (0.3); 0.4374 (0.1); 0.3496 (0.1); 0.3420 (0.2); 0.3336 (0.3);0.3259 (0.4); 0.3209 (0.3); 0.3083 (0.3); 0.2991 (0.4); 0.2929 (0.7);0.2851 (0.9); 0.2777 (0.8); 0.2702 (0.8); 0.2622 (1.1); 0.2528 (1.0);0.2459 (0.9); 0.2398 (1.0); 0.2322 (0.7); 0.2254 (0.4); 0.2170 (0.2);0.0967 (0.4); 0.0109 (0.2); 0.0054 (2.2); −0.0001 (84.9); −0.0057 (3.1);−0.0124 (1.5); −0.0265 (0.1); −0.0319 (0.1); −0.0376 (0.1); −0.0430(0.1); −0.0580 (0.1); −0.0820 (0.1); −0.1002 (0.4); −0.1791 (0.3);−0.1875 (0.7); −0.1954 (1.0).

ESI mass [m/z]: 461.1 [M+H]⁺

Synthesis ofN-(cyclopropylmethyl)-N-{1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-[(trifluoromethyl)sulfonyl]benzamide(example I-005)

A mixture of 50 mg (111μmol)N-(cyclopropylmethyl)-N-{1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-[(trifluoromethyl)sulfanyl]benzamide,2 mL dichloromethane, 2 mL acetonitrile and 4 mL water was treated with72 mg (0.33 mmol) sodium periodate followed by 0.02 mg (0.1 μmol)ruthenium(III) chloride. The reaction mixture was stirred at roomtemperature for 1.5 h. Water and dichloromethane were added, the layersseparated and the aqueous layer was extracted several times withdichloromethane. The combined organic layers were dried with Na₂SO₄,filtered and concentrated under reduced pressure to provide 20 mg ofN-(cyclopropylmethyl)-N-{1-[1-(pyrimidin-2-yl)-H-1,2,4-triazol-5-yl]ethyl}-3-[(trifluoromethyl)sulfonyl]benzamide.

¹H-NMR (600.1 MHz, CD₃CN, 260 K): NMR peaklist: δ=9.0235 (0.2); 9.0154(0.1); 8.9241 (0.4); 8.9161 (0.4); 8.9092 (0.3); 8.9011 (0.4); 8.8879(0.9); 8.8764 (12.2); 8.8684 (12.2); 8.7211 (0.1); 8.7130 (0.1); 8.5912(0.3); 8.5831 (0.5); 8.5723 (2.6); 8.5645 (2.6); 8.4517 (0.1); 8.3799(0.1); 8.2586 (0.1); 8.2337 (0.1); 8.2199 (0.1); 8.1799 (0.2); 8.1638(0.2); 8.1513 (0.1); 8.1383 (0.1); 8.1122 (3.6); 8.0990 (4.0); 8.0877(11.2); 8.0726 (0.8); 8.0596 (0.6); 8.0393 (2.6); 8.0250 (1.0); 8.0122(1.0); 7.9954 (0.1); 7.9814 (0.1); 7.9643 (0.1); 7.9586 (0.1); 7.9462(0.2); 7.9321 (0.2); 7.9115 (1.8); 7.8855 (0.1); 7.8806 (0.1); 7.8713(0.1); 7.8636 (0.1); 7.8547 (0.1); 7.7884 (2.8); 7.7754 (5.8); 7.7623(3.3); 7.7223 (0.6); 7.7106 (1.6); 7.7034 (1.4); 7.6904 (1.3); 7.6755(4.9); 7.6624 (3.7); 7.6295 (6.8); 7.6139 (0.1); 7.5380 (0.2); 7.5276(0.3); 7.5165 (3.4); 7.5084 (6.4); 7.5004 (3.2); 7.4879 (0.2); 7.4743(0.2); 7.4507 (0.5); 7.4369 (0.4); 7.3810 (0.9); 7.3734 (1.4); 7.3656(0.7); 6.5009 (0.1); 6.4358 (0.1); 6.4239 (0.2); 6.4066 (1.2); 6.3951(3.8); 6.3835 (3.8); 6.3719 (1.2); 6.2934 (0.1); 6.2818 (0.1); 6.1368(0.1); 6.1334 (0.1); 6.0337 (0.3); 6.0227 (0.9); 6.0113 (0.9); 6.0002(0.3); 5.9466 (0.1); 5.9354 (0.1); 5.6189 (0.1); 5.6035 (0.1); 5.4721(9.8); 5.3607 (0.3); 5.3524 (0.5); 5.3443 (0.3); 5.3369 (0.1); 5.3189(0.1); 3.7124 (0.1); 3.6988 (0.1); 3.6872 (0.6); 3.6767 (0.6); 3.6635(0.7); 3.6531 (0.7); 3.5619 (0.1); 3.5496 (0.1); 3.5375 (0.1); 3.4961(0.7); 3.4845 (0.7); 3.4722 (0.6); 3.4607 (0.6); 3.4443 (0.1); 3.4363(0.1); 3.4337 (0.1); 3.4258 (0.1); 3.2372 (0.1); 3.2270 (0.1); 3.2162(0.1); 3.1097 (0.1); 3.0986 (0.1); 3.0329 (0.5); 3.0220 (0.8); 3.0115(0.5); 3.0015 (0.1); 2.9900 (0.2); 2.9792 (0.1); 2.9472 (0.1); 2.9183(0.3); 2.9104 (0.3); 2.8935 (0.1); 2.8817 (0.1); 2.8719 (0.3); 2.8671(0.3); 2.8612 (0.3); 2.8454 (9.0); 2.8349 (9.8); 2.8193 (0.4); 2.8088(0.1); 2.8035 (0.1); 2.7934 (0.1); 2.7793 (0.1); 2.7300 (0.5); 2.6637(0.6); 2.5973 (0.1); 2.3290 (0.1); 2.3232 (0.1); 2.3147 (0.2); 2.2914(121.5); 2.2685 (0.2); 2.2560 (0.3); 2.2479 (0.1); 2.2427 (0.1); 2.1918(0.1); 2.1103 (0.5); 2.0978 (1.0); 2.0851 (0.6); 2.0801 (0.4); 2.0760(0.7); 2.0719 (1.0); 2.0678 (0.7); 2.0637 (0.4); 2.0497 (0.1); 2.0456(0.1); 2.0324 (0.2); 2.0210 (0.6); 2.0114 (0.6); 2.0001 (0.4); 1.9925(0.2); 1.9852 (1.6); 1.9771 (2.6); 1.9692 (61.6); 1.9651 (119.3); 1.9610(175.6); 1.9569 (122.8); 1.9529 (63.2); 1.9354 (0.3); 1.9262 (0.2);1.9229 (0.2); 1.9180 (0.2); 1.8958 (0.1); 1.8917 (0.1); 1.8870 (0.1);1.8830 (0.1); 1.8780 (0.1); 1.8736 (0.1); 1.8687 (0.1); 1.8540 (0.5);1.8501 (0.8); 1.8459 (1.2); 1.8418 (1.1); 1.8292 (15.8); 1.8176 (16.0);1.7871 (0.2); 1.7838 (0.2); 1.7491 (3.9); 1.7377 (3.8); 1.7109 (0.2);1.7000 (0.1); 1.6931 (0.1); 1.6813 (0.1); 1.6756 (0.1); 1.6602 (0.1);1.6408 (0.1); 1.6271 (0.1); 1.6043 (0.1); 1.5882 (0.1); 1.5350 (0.2);1.5249 (0.6); 1.5134 (0.6); 1.5001 (0.3); 1.4780 (0.1); 1.4701 (0.1);1.4580 (0.1); 1.4486 (0.1); 1.4441 (0.1); 1.4279 (0.1); 1.4208 (0.1);1.4108 (0.4); 1.4029 (0.2); 1.3906 (0.2); 1.3771 (0.1); 1.3630 (0.2);1.3517 (0.2); 1.3408 (0.9); 1.3086 (0.8); 1.2826 (2.9); 1.2601 (9.1);1.2169 (0.2); 1.2069 (0.2); 1.1912 (0.4); 1.1758 (0.2); 1.1598 (0.2);1.1519 (0.1); 1.1420 (0.1); 1.1358 (0.1); 1.1246 (0.4); 1.1098 (0.1);1.0974 (0.1); 1.0942 (0.1); 1.0852 (0.5); 1.0737 (1.6); 1.0617 (0.4);1.0506 (0.6); 1.0463 (1.8); 1.0403 (1.6); 1.0294 (1.5); 1.0204 (0.9);0.9820 (0.1); 0.9688 (0.2); 0.9578 (0.2); 0.9493 (0.2); 0.9452 (0.2);0.9372 (0.2); 0.9327 (0.2); 0.9246 (0.3); 0.9168 (0.2); 0.9124 (0.2);0.8927 (1.1); 0.8816 (2.2); 0.8697 (1.2); 0.8528 (0.5); 0.8404 (0.3);0.8151 (0.1); 0.8045 (0.2); 0.7922 (0.1); 0.7816 (0.1); 0.7654 (0.1);0.5550 (0.2); 0.5415 (0.7); 0.5320 (1.6); 0.5225 (2.2); 0.5121 (1.7);0.4997 (0.9); 0.4890 (0.5); 0.4801 (0.6); 0.4641 (1.1); 0.4570 (1.5);0.4434 (1.2); 0.4346 (0.7); 0.4222 (0.2); 0.3916 (0.1); 0.3844 (0.1);0.3712 (0.1); 0.3638 (0.1); 0.3564 (0.1); 0.3392 (0.3); 0.3317 (0.5);0.3236 (0.7); 0.3157 (0.8); 0.2837 (0.1); 0.2734 (0.2); 0.2602 (0.6);0.2515 (1.0); 0.2451 (1.9); 0.2369 (2.6); 0.2299 (2.7); 0.2228 (2.4);0.2150 (2.9); 0.2066 (2.4); 0.1995 (2.3); 0.1932 (2.5); 0.1842 (2.0);0.1721 (1.0); 0.0970 (0.1); 0.0786 (0.2); 0.0243 (0.1); 0.0183 (0.1);0.0054 (0.6); −0.0001 (19.3); −0.1005 (0.1); −0.2529 (0.8); −0.2613(1.9); −0.2693 (2.7); −0.2772 (2.8); −0.2847 (2.1); −0.2926 (0.8);−0.4435 (0.9); −0.4514 (2.2); −0.4590 (2.8); −0.4670 (2.6); −0.4751(1.8); −0.4833 (0.7).

ESI mass [m/z]: 481.1 [M+H]⁺

3-Chloro-5-(cyclopropylcarbamoyl)benzoic acid

A solution of 0.80 g (3.98 mmol) 5-chloroisophthalic acid, 1.82 g (4.78mmol) 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium3-oxid hexafluorophosphate (HATU) and 0.83 mL (4.8 mL)N,N-diisopropylethylamine in dichloromethane was stirred for 10 min aroom temperature and then treated with 0.28 mL (4.0 mmol)cyclopropylamine. The mixture was stirred over night at roomtemperature. The solvent was evaporated under reduced pressure and theresidue purified by HPLC (H₂O/acetonitrile) to provide 286 mg of3-chloro-5-(cyclopropylcarbamoyl)benzoic acid.

¹H-NMR (400.2 MHz, d₆-DMSO): NMR peaklist; δ=13.5637 (0.4); 8.7486(4.5); 8.7384 (4.5); 8.6590 (0.4); 8.6491 (0.4); 8.3479 (8.7); 8.3442(16.0); 8.3404 (9.1); 8.2041 (0.6); 8.2002 (0.3); 8.1020 (8.3); 8.0971(12.8); 8.0928 (9.1); 8.0221 (9.5); 8.0184 (11.4); 8.0172 (11.0); 8.0133(8.3); 7.9664 (1.2); 7.9626 (1.2); 3.3349 (4.9); 2.9095 (0.7); 2.8993(2.1); 2.8895 (2.8); 2.8811 (4.6); 2.8709 (4.7); 2.8629 (2.8); 2.8528(2.3); 2.8426 (0.9); 2.6789 (0.4); 2.6744 (0.6); 2.6698 (0.4); 2.5278(1.6); 2.5230 (2.6); 2.5144 (35.4); 2.5099 (72.7); 2.5053 (95.3); 2.5007(67.5); 2.4962 (31.8); 2.3368 (0.4); 2.3321 (0.6); 2.3276 (0.4); 2.0772(5.6); 0.7363 (2.8); 0.7234 (6.7); 0.7181 (10.9); 0.7065 (9.2); 0.6996(8.1); 0.6889 (4.3); 0.6683 (0.8); 0.6587 (0.7); 0.6501 (1.1); 0.6197(4.2); 0.6093 (11.3); 0.6012 (9.3); 0.5993 (9.0); 0.5943 (6.9); 0.5915(6.9); 0.5809 (3.0); 0.1459 (0.4); 0.0133 (0.3); 0.0079 (3.6); −0.0002(107.9); −0.0086 (3.6); −0.1497 (0.4).

ESI mass [m/z]: 240.2 [M+H]⁺

4′-Fluoro-5-(trifluoromethyl)[biphenyl]-3-carboxylic acid

A mixture of 400 mg (1.48 mmol) 3-bromo-5-(trifluoromethyl)benzoic acid,250 mg (1.78 mmol) (4-fluorophenyl)boronic acid, 109 mg (140 μmol)[1,1′-bis(diphenylphosphino)ferrocene].-dichloropalladium(II), 969 mg(2.97 mmol) cesium carbonate, 3.1 mL 1,4-dioxane and 0.75 mL ethanol washeated for 2 h at 80° C. The reaction mixture was then filtered overcelite washing with ethanol. The filtrate was concentrated under reducedpressure, treated with 1 M aqeuous HCl and extracted several times withethyl acetate. The combined organic layers were washed with brine, driedwith Na₂SO₄ and concentrated under reduced pressure. The residue wasrecrystallized from dichloromethane yielding 316 mg4′-fluoro-5-(trifluoromethyl)[biphenyl]-3-carboxylic acid.

¹H-NMR (400.2 MHz, d₆-DMSO): NMR peaklist: δ=13.6540 (1.8); 8.4111(10.5); 8.2400 (9.6); 8.1578 (10.0); 7.8932 (7.8); 7.8882 (3.7); 7.8798(8.7); 7.8713 (9.3); 7.8630 (3.8); 7.8579 (8.3); 7.8503 (1.0); 7.3862(1.0); 7.3785 (8.5); 7.3564 (16.0); 7.3393 (2.8); 7.3343 (7.7); 7.3269(0.9); 4.0389 (0.5); 4.0211 (0.5); 3.3310 (18.2); 2.6778 (0.8); 2.6734(1.0); 2.6693 (0.8); 2.5090 (131.2); 2.5046 (168.3); 2.5002 (125.9);2.3357 (0.8); 2.3313 (1.0); 2.3271 (0.8); 1.9902 (2.0); 1.1940 (0.5);1.1762 (1.1); 1.1584 (0.5); 0.1460 (0.5); 0.0077 (4.5); −0.0002 (100.7);−0.0083 (4.6); −0.1496 (0.5).

ESI mass [m/z]: 283.1 [M−H]⁻

Methyl 3-cyclopropyl-5-(trifluoromethyl)benzoate

A mixture of 1.00 g (3.53 mmol) methyl3-bromo-5-(trifluoromethyl)benzoate, 334 mg (3.88 mmol)cyclopropylboronic acid, 891 mg (10.6 mmol) NaHCO₃ in 8 mL 1,4-dioxaneand 4 mL H₂O was degassed by purging with argon. 129 mg (176 μmol)[1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) were added.The mixture was degassed once more by purging with argon before it washeated for 10 h at 100° C. The mixture was concentrated under reducedpressure. Water and dichloromethane were added, the layers separated andthe aqueous layer was extracted several times with dichloromethane. Thecombined organic layers were dried with Na₂SO₄, filtered andconcentrated under reduced pressure. The residue was purified by HPLC(H₂O/acetonitrile) to provide 23 mg of methyl3-cyclopropyl-5-(trifluoromethyl)benzoate.

¹H-NMR (400.2 MHz, d₆-DMSO): NMR peaklist: δ=7.9431 (2.1); 7.8956 (2.3);7.7295 (2.1); 3.8896 (16.0); 3.8753 (0.6); 3.3255 (10.1); 2.5264 (0.4);2.5129 (8.4); 2.5088 (16.6); 2.5043 (21.5); 2.4998 (15.6); 2.4956 (7.8);2.2086 (0.6); 2.2002 (0.6); 2.1965 (0.4); 2.1877 (1.2); 2.1752 (0.7);2.1667 (0.6); 1.0928 (0.7); 1.0813 (1.9); 1.0759 (2.0); 1.0650 (1.0);1.0603 (2.0); 1.0549 (1.9); 1.0442 (0.8); 0.8501 (0.8); 0.8387 (2.3);0.8340 (2.1); 0.8267 (2.0); 0.8216 (2.4); 0.8098 (0.7); 0.0078 (0.5);−0.0002 (13.4); −0.0082 (0.6).

ESI mass [m/z]: 245.1 [M]⁺

Synthesis of 3-chloro-5-[(trifluoromethyl)sulfanyl]benzoic acid Step 1:[3-chloro-5-(methoxycarbonyl)phenyl]boronic acid

To a suspension of 12 g (40 mmol) methyl3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate in 30mL acetone and 30 mL H₂O were added 17.3 g (80.9 mmol) sodium periodateand 6.24 g (80.9 mmol) ammonium acetate. The mixture was stirred at 25°C. for 2 h and then filtered through celite. The filtrate wasevaporated. The residue was diluted with 200 mL ethyl acetate and washedwith 100 mL H₂O. The organic phase was washed with brine, dried overanhydrous Na₂SO₄, filtered and concentrated in vacuum. The crude productwas triturated with 10 mL petroleum ether at 15° C. for 20 min. Themixture was filtered and the residue dried under reduced pressure toobtain 7 g [3-Chloro-5-(methoxycarbonyl)phenyl]boronic acid as a whitesolid.

¹H-NMR (400 MHz, CDCl₃): δ=8.72 (s, 1H), 8.35 (s, 1H), 8.27 (s, 1H),4.02 (s, 3H). Referenced to the signal of trace CHCl₃ at 7.25 ppm.Measured using a Varian 400MR NMR machine.

Step 2: methyl 3-chloro-5-[(trifluoromethyl)sulfanyl]benzoate

13 g (61 mmol) [3-Chloro-5-(methoxycarbonyl)phenyl]boronic acid, 43.1 g(303 mmol) trimethyl(trifluoromethyl)silane, 33.4 g (121 mmol) Ag₂CO₃,38.6 g (182 mmol) K₃PO₄, 762 mg (6.06 mmol) CuSCN, 2.2 g (12 mmol)1,10-Phenanthroline, 46.7 g (1.46 mol) sulfur and 13 g 4 A molecularsieves in 500 mL DMF were stirred at 25° C. for 16 h under N₂. Themixture was filtered through celite. The filtrate was diluted with 1.5 Lmethyl tert-butyl ether and washed with 2×500 mL H₂O. The organic phasewas washed with brine, dried over anhydrous Na₂SO₄, filtered andconcentrated in vacuum. The crude product was purified by MPLC on silicagel (petroleum ether:ethyl acetate=1:0 20:1) to obtain 5.5 g methyl3-chloro-5-[(trifluoromethyl)sulfanyl]benzoate as a light yellow oil.

¹H-NMR (400 MHz, CDCl₃): δ=8.20 (s, 1H), 8.10-8.15 (m, 1H), 7.83 (s,1H), 3.96 (s, 3H). Referenced to the signal of trace CHCl₃ at 7.25 ppm.Measured using a Varian 400MR NMR machine.

Step 3: 3-chloro-5-[(trifluoromethyl)sulfanyl]benzoic acid

5.5 g (20 mmol) Methyl 3-chloro-5-[(trifluoromethyl)sulfanyl]benzoatewere dissolved in a mixture of 12 mL tetrahydrofuran and 12 mL H₂O. 1.63g (40.6 mmol) NaOH were added to the mixture which was then stirred at25° C. for 2 h. The mixture was adjusted to pH 5 by addition of 40 mL 1M HCl and extracted with 150 mL ethyl acetate. The organic phase waswashed with brine, dried over anhydrous Na₂SO₄, filtered andconcentrated in vacuum. The crude product was triturated with 50 mLpetroleum ether at 25° C. for 15 min. The mixture was filtered and theresidue dried under reduced pressure to obtain 3.0 g3-chloro-5-(trifluoromethylsulfanyl)benzoic acid as a yellow solid.

¹H-NMR (400 MHz, CDCl₃): δ=11.28 (br s, 1H), 8.29 (s, 1H), 8.20-8.25 (m,1H), 7.91 (s, 1H). Referenced to the signal of trace CHCl₃ at 7.25 ppm.Measured using a Varian 400MR NMR machine.

ESI mass [m/z]: 254.8 [M−H]⁻

The determination by LC-MS was carried out using the mobile phasesacetonitrile and 10 mM aqueous ammonium bicarbonate solution; lineargradient from 15% acetonitrile to 90% acetonitrile, flow rate 0.80ml/min; instruments: Agilent 1200 & Agilent 6120. The column used forchromatography was a 2.1*50 mm Xbridge Shield RPC18 column (5 μmparticles). Detection methods are diode array (DAD) and evaporativelight scattering (ELSD) detection as well as negative electrosprayionization.

Synthesis of3-chloro-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-[(trifluoromethyl)sulfonyl]benzamide(example I-033) Step 1: 3-chloro-5-[(trifluoromethyl)sulfonyl]benzoicacid

1 g (3.89 mmol) 3-chloro-5-[(trifluoromethyl)sulfanyl]benzoic acid wasdissolved in a mixture of 20 mL dichloromethane, 20 mL acetonitrile and20 mL of water. 2.5 g (11.6 mmol) sodium periodate and 0.81 mg (3.9μmol) ruthenium(III) chloride were added to the mixture which was thenstirred at room temperature for 90 min. The mixture was diluted by theaddition of water and extracted with dichloromethane. The organic phasewas dried over anhydrous Na₂SO₄, filtered and concentrated in vacuo toobtain 1.2 g of the title compound as a colorless solid. The crudeproduct was used as such in the next step.

¹H-NMR (400 MHz, d₆-DMSO): δ=14.27-14.20 (br s, 1H), 8.51 (s, 1H), 8.49(s, 1H), 8.38 (s, 1H).

ESI mass [m/z]: 287.0 [M−H]⁻

Step 2:N-[(2S)-1-amino-1-oxopropan-2-yl]-3-chloro-5-[(trifluoromethyl)sulfonyl]benzamide

1.2 g (crude from step 1, 4.15 mmol) were dissolved in 20 mLdichloromethane, two drops of DMF and 0.43 mL (4.98 mmol) oxalylchloride were added. The mixture was stirred for 5 h at roomtemperature. Dichloromethane and excess oxalyl chloride were removedunder reduced pressure and the remaining residue was diluted with 50 mLdichloromethane and 1.03 g (8.3 mmol) (2S)-2-aminopropanamidehydrochloride were added. 2.31 mL (16 mmol) triethylamine were addeddropwise within 5 minutes. The mixture was stirred at room temperaturefor 1 h, monitored by thin layer chromatography. The mixture wasconcentrated in vacuo, diluted with water and extracted withdichloromethane. The organic phase was dried over anhydrous Na₂SO₄,filtered and concentrated in vacuo. The remaining residue was purifiedby chromatography (gradient cyclohexane/ethyl acetate) to obtain 1.1 gof the title compound as a colorless solid.

¹H NMR (400 MHz, d6-DMSO): δ=9.13-9.11 (d, 1H, NH), 8.61 (s, 1H), 8.54(s, 1H), 8.41 (s, 1H), 7.50 (br s, 1H from NH₂), 7.05 (br s, 1H fromNH₂), 4.46-4.39 (m, 1H), 1.36-1.35 (d, 3H).

ESI mass [m/z]: 358.9 [M+H]⁺

Step 3:3-chloro-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-[(trifluoromethyl)sulfonyl]benzamide (example I-033)

1.1 g (81.6% purity, 2.53 mmol) ofN-[(2S)-1-aminoamino-1-oxopropan-2-yl]-3-chloro-5-[(trifluoromethyl)sulfonyl]benzamidewere dissolved in 20 mL dichloromethane. 447 mg (3.75 mmol)N,N-dimethylformamide dimethyl acetal were added, and the reactionmixture was refluxed for 90 minutes. The solvents were removed underreduced pressure, and the remaining residue was dissolved in a mixtureof 20 mL dioxane and 3 mL acetic acid. 336 mg (3.05 mmol)2-hydrazinopyrimidine were added. The reaction mixture was stirred overnight at 50° C., concentrated in vacuo and diluted with water and ethylacetate. The separated organic phase was washed with aqueous sodiumbicarbonate, dried over anhydrous Na₂SO₄, filtered and concentrated invacuo. The remaining residue was purified by pHPLC to obtain 0.3 g3-chloro-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-[(trifluoromethyl)sulfonyl]benzamideas a colorless solid.

¹H-NMR (400 MHz, d6-DMSO): see NMR peak list in table 1.

ESI mass [m/z]: 460.9 [M+H]⁺

Synthesis of3-chloro-5-(methylsulfonyl)-N-{1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamide(example I-020)

4.00 g (11.8 mmol) 2-[5-(I-bromoethyl)-1H-1,2,4-triazol-1-yl]pyrimidinewere treated with 40 mL of an ammonia solution in methanol (7 M, 0.3mol). The mixture was stirred overnight at room temperature. Then anadditional 20 mL of ammonia solution in methanol (7 M, 0.14 mol) wereadded and stirring was continued until complete conversion of thestarting material was observed by HPLC analysis. The reaction mixturewas concentrated under reduced pressure and the residue used withoutfurther purification.

To 136 mg (580 μmol) 3-chloro-5-(methylsulfonyl)benzoic acid were added5 mL acetonitrile, 365 mg (960 μmol)1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium3-oxid hexafluorophosphate (HATU) and 0.19 mL (1.4 mmol)N,N-diisopropylethylamine. The mixture was stirred for 1 h at roomtemperature. Then 200 mg of the residue containing1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethanamine from the previousstep were added. The reaction mixture was stirred over night at roomtemperature before it was purified by HPLC (H₂O/acetonitrile) to provide64 mg of3-chloro-5-(methylsulfonyl)-N-{1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamide.

¹H-NMR (400 MHz, d₆-DMSO): see NMR peak list in table 1.

ESI mass [m/z]: 407.1 [M+H]⁺

Synthesis of (1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethanaminehydrochloride Step 1: tert-butyl{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}carbamate

To a solution of 4.78 g (25.3 mmol)N²-(tert-butoxycarbonyl)-L-alaninamide in 100 mL CH₂Cl₂ was added 4.97mL (37.5 mmol) N,N-dimethylformamide dimethylacetal. The solution washeated at reflux for 2 h after which the solvent was removed in vacuuo.The residue was dissolved in a mixture of 45 mL 1,4-dioxane and 45 mLglacial acetic acid. 3.41 g (31 mmol) 2-hydrazinopyrimidine were addedand the mixture stirred at 50° C. for 45 min. The solvents were removedunder reduced pressure, a saturated aqueous solution of NaHCO₃ was addedand the mixture repeatedly extracted with ethyl acetate. The combinedorganic layers were dried with Na₂SO₄ and the solvent was removed underreduced pressure. The residue was purified by reversed phasechromatography (H₂O/acetonitrile) to provide 4.51 g of tert-butyl{(1S)-1-[1-(pyrimidin-2-yl)-H-1,2,4-triazol-5-yl]ethyl}carbamate.

[α]_(D) ²⁰=+82 (c=0.95; ethanol)

¹H NMR (DMSO-d₆, 400 MHz): NMR peaklist: δ=9.0011 (3.9); 8.9890 (3.9);8.1196 (2.5); 7.6599 (2.2); 7.6477 (4.2); 7.6356 (2.1); 7.4658 (0.7);7.4465 (0.7); 5.5270 (0.5); 5.5091 (0.7); 5.4910 (0.5); 3.3264 (15.3);2.5262 (0.3); 2.5214 (0.6); 2.5127 (8.5); 2.5083 (17.6); 2.5037 (23.5);2.4992 (17.0); 2.4948 (8.1); 2.0759 (10.4); 1.4486 (3.8); 1.4312 (3.5);1.2827 (16.0); 1.0275 (0.9); −0.0002 (7.8).

ESI mass [m/z]: 235.2 [M-C₄H₈+H]⁺

Step 2: (1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethanaminehydrochloride

To a solution of 2.0 g (6.9 mmol) tert-butyl{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}carbamate in 40mL 1,4-dioxane were added 17 mL of a 4 M solution of HCl in 1,4-dioxane.The mixture was stirred for 4 h at 50° C. and overnight at roomtemperature. The solvent was removed under reduced pressure to provide1.74 g of a residue containing(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethanaminehydrochloride. This was used without further purification.

¹H NMR (DMSO-d₆, 400 MHz): NMR peaklist: δ=9.0360 (15.7); 9.0238 (16.0);8.7967 (0.4); 8.7061 (3.5); 8.3670 (13.0); 7.6975 (4.2); 7.6853 (8.0);7.6731 (4.1); 5.3554 (0.4); 5.3411 (1.2); 5.3263 (1.5); 5.3108 (1.2);5.2960 (0.5); 4.1434 (0.4); 4.1253 (0.8); 4.1107 (2.1); 4.0899 (0.4);4.0210 (1.2); 3.8777 (0.9); 3.8698 (0.8); 3.8623 (0.9); 3.8418 (0.8);3.8335 (0.7); 3.8212 (0.6); 3.7300 (0.3); 3.7252 (0.3); 3.7144 (0.5);3.7104 (0.4); 3.7006 (0.6); 3.6806 (0.6); 3.6709 (0.4); 3.6668 (0.5);3.5683 (5.6); 3.5139 (0.3); 3.5048 (1.1); 3.4994 (1.5); 3.4958 (1.6);3.4903 (1.5); 3.4837 (0.4); 3.4742 (0.6); 3.4660 (0.9); 3.4486 (2.4);3.4311 (2.4); 3.4136 (0.8); 3.3886 (3.4); 2.6770 (0.5); 2.6725 (0.6);2.6681 (0.5); 2.5259 (1.8); 2.5212 (2.8); 2.5125 (38.7); 2.5081 (79.6);2.5036 (104.8); 2.4990 (74.8); 2.4946 (35.9); 2.3350 (0.4); 2.3303(0.6); 2.3260 (0.5); 1.6495 (14.5); 1.6327 (14.3); 1.5476 (0.6); 1.5305(0.6); 1.2164 (0.8); 1.1985 (1.7); 1.1808 (0.8); 1.1400 (0.4); 1.0728(2.4); 1.0554 (4.7); 1.0379 (2.3); −0.0001 (4.9).

ESI mass [m/z]: 191.2 [M+H]⁺

Synthesis of3-chloro-N-ethyl-5-(methylsulfonyl)-N-{1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamide(example I-040) Step 1:N-ethyl-1-[1-(pyrimidin-2-yl)-H-1,2,4-triazol-5-yl]ethanamine

500 mg (1.86 mmol) of2-[5-(1-bromoethyl)-1H-1,2,4-triazol-1-yl]pyrimidine (known from WO2017192385) were dissolved in 30 mL acetonitrile. Then 775 mg (5.60mmol) potassium carbonate and 1.87 mL of a 2M solution of ethylamine inTHF were added. The reaction mixture was heated to reflux for two hours.After cooling, the reaction mixture was filtered via Celite®, the filtercake was washed with acetonitrile and the filtrate was evaporated underreduced pressure to obtain 450 mg of the title compound which was usedas such in the next step.

¹H NMR (DMSO-d₆, 400 MHz): 9.00-8.99 (d, 2H), 8.14 (s, 1H), 7.66-7.64(t, 1H), 4.67-4.57 (broad m, 1H), 2.34-2.31 (broad m, 2H), 2.04 (broads, 1H, NH), 1.40-1.38 (d, 3H), 0.86-0.82 (t, 3H).

ESI mass [m/z]: 219.3 [M+H]⁺

Step 2:3-chloro-N-ethyl-5-(methylsulfonyl)-N-{1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamide(example I-040)

449 mg (1.77 mmol) ofN-ethyl-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethanamine weredissolved in 20 mL acetonitrile followed by 0.462 mL (2.65 mmol) DIPEA.To this reaction mixture, 448 mg (1.77 mmol) of3-chloro-5-(methylsulfonyl)benzoyl chloride dissolved in 21 mLacetonitrile were added drop wise. The reaction mixture was stirred atroom temperature over night, followed by evaporation of the solventunder reduced pressure. The title compound was obtained afterpurification by reversed phase chromatography (H₂O/acetonitrile). Yield:470 mg (yield: 61%).

¹H NMR (DMSO-d₆, 400 MHz, 260K): see NMR peak list in table 1.

ESI mass [m/z]: 435.1 [M+H]⁺

Synthesis of3-chloro-5-(ethylsulfonyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamide(example I-044) Step 1: 3-chloro-5-(ethylsulfonyl)benzoic acid

A mixture of 0.47 g (4.1 mmol) proline and 0.16 g (4.0 mmol) sodiumhydroxide in 24 mL dimethylsulfoxide was degassed for 30 min by purgingwith argon. 1.5 g (5.1 mmol) methyl 3-chloro-5-iodobenzoate, 4.7 g (40mmol) sodium ethanesulfinate and 0.77 g (4.0 mmol) copper(I) iodide wereadded and the mixture further purged with argon for 5 min. The mixturewas stirred at 120° C. for 3 h, cooled to room temperature and thentreated with 4 mL of a 2 M aqeuous sodium hydroxide solution. It wasfurther stirred over night at room temperature, cooled to 10° C. andacidified to pH 1 using concentrated hydrochloric acid. Water was addedto the mixture and it was extracted with ethyl acetate. The layers wereseparated and the aqueous layer repeatedly extracted with ethyl acetate.The combined organic layers were washed twice with water and once withbrine and then dried with Na₂SO₄. The solvent was removed under reducedpressure and the residue purified by reversed phase chromatography(H₂O/acetonitrile) to provide 1.00 g of3-chloro-5-(ethylsulfonyl)benzoic acid.

¹H NMR (DMSO-d₆, 400 MHz): NMR peaklist: δ=8.2775 (3.5); 8.2737 (6.8);8.2698 (4.4); 8.2363 (3.4); 8.2325 (4.0); 8.2313 (5.4); 8.2277 (4.1);8.2090 (4.8); 8.2046 (5.5); 8.1997 (3.0); 3.4891 (1.9); 3.4707 (6.7);3.4523 (6.8); 3.4340 (2.1); 3.3298 (6.3); 2.5259 (0.6); 2.5212 (1.0);2.5125 (17.2); 2.5080 (36.2); 2.5034 (48.0); 2.4988 (33.7); 2.4942(15.6); 1.1402 (6.9); 1.1219 (16.0); 1.1034 (6.8); −0.0002 (5.1).

ESI mass [m/z]: 247.1 [M−H]⁻

Step 2:3-chloro-5-(ethylsulfonyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benz-amide(example I-044)

To 369 mg (1.48 mmol) of 3-chloro-5-(ethylsulfonyl)benzoic acid wereadded 10 mL acetonitrile, 936 mg (2.47 mmol)N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uroniumhexafluorophosphate (HBTU) and 0.48 mL (3.7 mmol)N,N-diisopropylethylamine. The mixture was stirred for 1 h a roomtemperature. Then 280 mg (1.23 mmol) of(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethanaminehydrochloride were added. The reaction mixture was stirred overnight atroom temperature before it was purified by reversed phase chromatography(H₂O/acetonitrile) to provide 270 mg of3-chloro-5-(ethylsulfonyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamide.

¹H-NMR (400 MHz, d₆-DMSO): see NMR peak list in table 1.

ESI mass [m/z]: 421.1 [M+H]⁺

Synthesis ofN-(cyclopropylmethyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-[(trifluoro-methyl)sulfonyl]benzamide(example I-047)

A solution of 100 mg (0.44 mmol)(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethanaminehydrochloride in 2.2 mL tetrahydrofuran was treated with 31 μL (0.41mmol) cyclopropanecarbaldehyde. After 5 min 140 mg (0.66 mmol) sodiumtriacetoxyborohydride were added and the mixture stirred over night atroom temperature. To the mixture were added 2 mL of a saturated aqueoussolution of NaHCO₃ and 2 mL ethyl acetate and stirring was continued for30 min. Another 10 mL aqueous saturated NaHCO₃ solution were added andthe mixture repeatedly extracted with ethyl acetate. The combinedorganic layers were dried with Na₂SO₄ and the solvent was removed underreduced pressure to provide 82 mg of a residue containing(1S)—N-(cyclopropylmethyl)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethanamine.

To the residue obtained in the previous step were added 69 mg (0.26mmol) 3-[(trifluoromethyl)sulfonyl]benzoic acid, 2.4 mL ethyl acetate,0.15 mL (0.85 mmol)N-ethyldiisopropylamine and 0.29 mL (0.41 mmol) of aT3P® solution (50 wt. % in EtOAc). The mixture was stirred over night atroom temperature. The solvent was removed under reduced pressure andresidue was purified by chromatography on silica (gradientcyclohexane/ethyl acetate) and by reversed phase chromatography(H₂O/acetonitrile) to provide 12 mgN-(cyclopropylmethyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-[(trifluoromethyl)sulfonyl]benzamide.

¹H-NMR (400 MHz, d₆-DMSO): see NMR peak list in table 1.

ESI mass [m/z]: 481.2 [M+H]⁺

Synthesis of3-chloro-5-(isopropylsulfonyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamide(example I-051) Step 1: 3-chloro-5-(isopropylsulfanyl)benzonitrile

A solution of 1.00 g (6.42 mmol) 3-chloro-5-fluorobenzonitrile and 820mg (8.35 mmol) sodium propane-2-thiolate in 20 mL N,N-dimethylformamidewas stirred over night at room temperature. To the mixture was added0.74 mL glacial acetic acid and the volatiles were removed under reducedpressure. Water and ethyl acetate were added to the residue. The layerswere separated and the aqueous layer repeatedly extracted with ethylacetate. The combined organic layers were washed with brine and thendried with Na₂SO₄. The solvent was removed under reduced pressure andthe residue purified by reversed phase chromatography (H₂O/acetonitrile)to provide 589 mg of 3-chloro-5-(isopropylsulfanyl)benzonitrile.

¹H-NMR (400 MHz, d₆-DMSO): NMR peaklist: δ=7.8514 (1.3); 7.8469 (2.2);7.8433 (1.7); 7.8148 (1.5); 7.8109 (2.7); 7.8075 (1.6); 7.7554 (1.7);7.7508 (2.7); 7.7464 (1.4); 3.8055 (0.4); 3.7890 (1.0); 3.7724 (1.4);3.7558 (1.0); 3.7393 (0.4); 3.3253 (10.3); 2.5215 (0.5); 2.5126 (6.3);2.5082 (12.9); 2.5037 (17.1); 2.4991 (12.2); 2.4946 (5.8); 1.2767(16.0); 1.2601 (15.5).

Step 2: 3-chloro-5-(isopropylsulfanyl)benzoic acid

To a solution of 585 mg (2.76 mmol)3-chloro-5-(isopropylsulfanyl)benzonitrile in 20 mL ethanol were added2.1 mL of a 50% aqueous solution of sodium hydroxide. The mixture washeated at reflux for 45 min. The volatiles were then removed underreduced pressure. Water was added, the pH adjusted to pH 1 by theaddition of 1 M hydrochloric acid and the mixture repeatedly extractedwith ethyl acetate. The combined organic layers were washed with brineand then dried with Na₂SO₄. The solvent was removed under reducedpressure to provide 610 mg of 3-chloro-5-(isopropylsulfanyl)benzoicacid.

¹H-NMR (400 MHz, d₆-DMSO): NMR peaklist: δ=7.7701 (1.6); 7.7662 (3.0);7.7624 (2.1); 7.7195 (1.7); 7.7146 (2.5); 7.7110 (2.0); 7.6738 (1.9);7.6691 (3.0); 7.6645 (1.5); 3.7020 (0.4); 3.6854 (1.1); 3.6688 (1.5);3.6522 (1.1); 3.6356 (0.4); 2.5160 (3.1); 2.5115 (6.7); 2.5069 (9.1);2.5023 (6.5); 2.4977 (3.1); 1.2786 (16.0); 1.2620 (15.4); −0.0002 (4.8).

ESI mass [m/z]: 231.1 [M+H]⁺

Step 3:3-chloro-5-(isopropylsulfanyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-benzamide(example I-046)

To 321 mg (1.39 mmol) of 3-chloro-5-(isopropylsulfanyl)benzoic acid wereadded 15 mL acetonitrile, 922 mg (2.43 mmol)N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uroniumhexafluorophosphate (HBTU) and 0.47 mL (3.6 mmol)N,N-diisopropylethylamine. The mixture was stirred for 1 h a roomtemperature. Then 315 mg (1.39 mmol) of(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethanaminehydrochloride were added. The reaction mixture was stirred over night atroom temperature before it was purified by reversed phase chromatography(H₂O/acetonitrile) to provide 302 mg of3-chloro-5-(isopropylsulfanyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamide.

¹H-NMR (400 MHz, d₆-DMSO): see NMR peak list in table 1.

ESI mass [m/z]: 403.2 [M+H]⁺

Step 4:3-chloro-5-(isopropylsulfonyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-benzamide(example I-051)

To a solution of 150 mg (0.37 mmol)3-chloro-5-(isopropylsulfanyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamidein 2 ml CH₂Cl₂ at 0° C. were added 193 mg (70% purity, 0.78 mmol)3-chloroperoxybenzoic acid. The reaction mixture was stirred for 2 h at0° C. after which a saturated aqueous NaHCO₃ solution was added. Thelayers were separated and the aqueous layer repeatedly extracted withCH₂Cl₂. The combined organic layers were washed with brine and thendried with Na₂SO₄. The solvent was removed under reduced pressure andthe residue purified by chromatography on silica (cyclohexane/ethylacetate) to provide 121 mg of3-chloro-5-(isopropylsulfonyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamide.

¹H-NMR (400 MHz, d₆-DMSO): see NMR peak list in table 1.

ESI mass [m/z]: 435.2 [M+H]⁺

3-chloro-5-cyclopropylbenzoic acid

A mixture of 1.00 g (3.37 mmol) methyl 3-chloro-5-iodobenzoate, 375 mg(4.36 mmol) cyclopropylboronic acid, 2.5 g (11.7 mmol) K₃PO₄, 95 mg(0.33 mmol) tricyclohexylphosphine in 20 mL toluene and 1 mL H₂O wasdegassed by purging with argon. 38 mg (0.16 mmol) palladium(II) acetatewere added. The mixture was heated for 3 h at 100° C. and over night atroom temperature. Another 290 mg (3.37 mmol) cyclopropylboronic acid and38 mg (0.16 mmol) palladium(II) acetate were added and the mixtureheated over night at reflux. Water and ethyl acetate were added, thelayers separated and the aqueous layer was extracted several times withethyl acetate. The combined organic layers were dried with Na₂SO₄,filtered and concentrated under reduced pressure. The residue waspurified by chromatography on silica (cyclohexane/ethyl acetate) andreversed phase chromatography (H₂O/acetonitrile) to provide 381 mg ofmethyl 3-chloro-5-cyclopropylbenzoate

A solution of 378 mg (1.79 mmol) methyl 3-chloro-5-cyclopropylbenzoatein 6 mL methanol was treated with 5 mL of a 1 M aqueous solution ofsodium hydroxide. The mixture was stirred over night at roomtemperature. The volatiles were then removed under reduced pressure.Water was added, the pH adjusted to pH 1 by the addition of 1 Mhydrochloric acid and the mixture repeatedly extracted with ethylacetate. The combined organic layers were dried with Na₂SO₄ and thesolvent removed under reduced pressure to provide 338 mg of3-chloro-5-cyclopropylbenzoic acid.

¹H-NMR (400 MHz, d₆-DMSO): NMR peak list: δ=13.2677 (3.0); 7.6530 (8.9);7.6483 (13.0); 7.6443 (10.4); 7.5890 (9.2); 7.5853 (16.0); 7.5815 (8.8);7.3987 (9.2); 7.3941 (15.6); 7.3894 (8.5); 3.3324 (4.4); 2.6744 (0.4);2.5279 (0.9); 2.5232 (1.4); 2.5145 (21.3); 2.5100 (43.8); 2.5055 (58.0);2.5009 (41.7); 2.4964 (19.9); 2.3323 (0.4); 2.0807 (1.5); 2.0681 (3.2);2.0597 (3.4); 2.0557 (2.2); 2.0472 (6.6); 2.0387 (2.2); 2.0346 (3.6);2.0262 (3.5); 2.0136 (1.7); 1.0376 (4.0); 1.0263 (10.8); 1.0209 (10.9);1.0170 (5.5); 1.0102 (5.6); 1.0053 (11.2); 0.9998 (10.4); 0.9893 (4.7);0.9726 (0.4); 0.9519 (0.4); 0.8186 (0.4); 0.8055 (0.4); 0.7809 (5.0);0.7699 (12.3); 0.7648 (12.0); 0.7575 (11.0); 0.7525 (13.4); 0.7409(4.0); −0.0002 (11.0); −0.0084 (0.3).

ESI mass [m/z]: 197.2 [M+H]⁺

Synthesis of1-(4-fluorophenyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide(example I-052) Step 1:1-(4-fluorophenyl)-3-(2-furyl)-5-(trifluoromethyl)-1H-pyrazole and1-(4-fluorophenyl)-5-(2-furyl)-3-(trifluoromethyl)-1H-pyrazole

To a solution of 1.00 g (4.85 mmol)4,4,4-trifluoro-1-(2-furyl)butane-1,3-dione in 15 mL ethanol were added2.1 mL (12 mmol) N,N-diisopropylethylamine and 1.18 g (7.3 mmol)(4-fluorophenyl)hydrazine hydrochloride. The mixture was stirred overnight at room temperature before all volatiles were removed underreduced pressure. To the residue were added water and ethyl acetate. Thelayers were separated and the aqueous layer was repeatedly extractedwith ethyl acetate. The combined organic layers were washed with brineand dried with Na₂SO₄. The solvent was removed under reduced pressure.The residue was dissolved in 15 mL tetrahydrofuran. 7 mL 3 Mhydrochloric acid were added and the mixture heated at 100° C. for 3 h.The solvent was then removed under reduced pressure. To the residue wereadded water and ethyl acetate. The layers were separated and the aqueouslayer was repeatedly extracted with ethyl acetate. The combined organiclayers were washed with brine and dried with Na₂SO₄. The solvent wasremoved under reduced pressure and the residue adsorbed onto reversedphase silica gel. Purification by reversed phase chromatography(H₂O/acetonitrile) provided 812 mg of an inseparable mixture of1-(4-fluorophenyl)-3-(2-furyl)-5-(trifluoromethyl)-1H-pyrazole and1-(4-fluorophenyl)-5-(2-furyl)-3-(trifluoromethyl)-1H-pyrazol.

¹H NMR (DMSO-d₆, 400 MHz): NMR peak list: δ=7.8066 (3.4); 7.8049 (3.4);7.8024 (3.4); 7.7757 (10.1); 7.7715 (10.0); 7.6722 (2.0); 7.6600 (2.3);7.6500 (2.7); 7.6380 (2.5); 7.6176 (0.9); 7.6092 (6.9); 7.6044 (3.2);7.5970 (7.6); 7.5921 (5.3); 7.5870 (9.1); 7.5797 (3.9); 7.5749 (8.5);7.5665 (1.0); 7.4735 (5.9); 7.4670 (3.4); 7.4452 (6.1); 7.4371 (9.2);7.4314 (3.4); 7.4230 (4.4); 7.4154 (14.7); 7.3985 (2.8); 7.3935 (6.7);7.3853 (0.8); 7.2688 (16.0); 6.9756 (3.1); 6.9672 (3.3); 6.6456 (2.3);6.6410 (2.4); 6.6374 (2.3); 6.6331 (2.0); 6.5590 (6.2); 6.5545 (6.6);6.5505 (6.8); 6.5462 (6.2); 6.2806 (9.5); 6.2719 (8.9); 3.3267 (119.8);2.6714 (1.0); 2.5065 (133.8); 2.5025 (166.0); 2.4984 (121.6); 2.3291(1.0); −0.0004 (25.2).

ESI mass [m/z]: 297.1 [M+H]⁺

Step 2: 1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylicacid and1-(4-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazole-3-carboxylicacid

777 mg (2.62 mmol) of the mixture of1-(4-fluorophenyl)-3-(2-furyl)-5-(trifluoromethyl)-1H-pyrazole and1-(4-fluorophenyl)-5-(2-furyl)-3-(trifluoromethyl)-1H-pyrazol obtainedin the previous step was dissolved in a mixture of 8 mL acetonitrile, 8ml CH₂Cl₂ and 12 mL water. To this mixture were added 54 mg (0.26 mmol)Ruthenium(III) chloride followed by 2.81 g (13.1 mmol) sodium periodate.The reaction mixture was stirred for 5 h at room temperature. 20 mL of 1M hydrochloric acid were added and the mixture filtered over celite,washing with ethyl acetate and water. The layers were separated and theaqueous layer repeatedly extracted with ethyl acetate. The combinedorganic layers were washed with brine and dried with Na₂SO₄. The solventwas removed under reduced pressure and the residue adsorbed ontoreversed phase silica gel. Purification by reversed phase chromatography(H₂O/acetonitrile) provided 101 mg1-(4-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazole-3-carboxylic acid in73% purity, 155 mg1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid in89% purity and another fraction of 139 mg1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid in98% purity.

1-(4-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazole-3-carboxylic

¹H NMR (DMSO-d₆, 400 MHz): NMR peak list δ=13.4416 (1.2); 8.3160 (0.6);7.7337 (0.4); 7.6983 (0.7); 7.6895 (6.2); 7.6775 (6.6); 7.6724 (4.4);7.6672 (7.8); 7.6552 (7.4); 7.6462 (0.9); 7.6362 (2.4); 7.6307 (0.9);7.6240 (2.5); 7.6190 (1.4); 7.6137 (2.9); 7.6071 (1.0); 7.6015 (2.7);7.5366 (16.0); 7.5245 (0.5); 7.5120 (0.4); 7.4912 (4.6); 7.4827 (10.2);7.4770 (3.0); 7.4701 (1.6); 7.4655 (3.6); 7.4610 (15.6); 7.4559 (3.4);7.4515 (1.2); 7.4445 (2.6); 7.4389 (7.9); 7.4302 (0.6); 7.3893 (0.3);7.3806 (2.9); 7.3751 (1.0); 7.3678 (0.5); 7.3588 (4.7); 7.3538 (1.1);7.3422 (0.8); 7.3367 (2.3); 5.7562 (2.2); 3.3275 (47.8); 2.6807 (0.5);2.6762 (1.0); 2.6717 (1.5); 2.6672 (1.1); 2.6625 (0.5); 2.5252 (4.4);2.5204 (6.8); 2.5117 (86.0); 2.5073 (173.8); 2.5028 (227.5); 2.4982(163.1); 2.4937 (78.4); 2.3386 (0.5); 2.3342 (1.0); 2.3296 (1.4); 2.3251(1.0); 2.3204 (0.5); 0.0080 (0.8); −0.0002 (26.3); −0.0085 (0.9).

ESI mass [m/z]: 275.1 [M+H]⁺

1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

¹H NMR (DMSO-d₆, 400 MHz): NMR peak list δ=8.3156 (0.4); 7.6460 (0.8);7.6373 (8.1); 7.6318 (2.9); 7.6251 (8.6); 7.6200 (4.9); 7.6147 (9.7);7.6081 (3.4); 7.6026 (9.2); 7.5939 (1.0); 7.5005 (16.0); 7.3903 (1.1);7.3816 (9.5); 7.3760 (2.9); 7.3687 (1.6); 7.3645 (3.3); 7.3597 (15.9);7.3547 (3.3); 7.3432 (2.6); 7.3377 (7.8); 7.3289 (0.7); 5.7558 (8.6);3.3341 (12.6); 2.6760 (0.7); 2.6714 (1.0); 2.6669 (0.7); 2.5249 (2.8);2.5201 (4.4); 2.5114 (60.4); 2.5070 (122.2); 2.5025 (160.1); 2.4979(115.0); 2.4935 (55.6); 2.3338 (0.7); 2.3293 (1.0); 2.3248 (0.7); 2.3202(0.4); 0.0080 (0.5); −0.0002 (17.5); −0.0085 (0.6).

ESI mass [m/z]: 275.1 [M+H]⁺

Step 3:1-(4-fluorophenyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-(trifluoro-methyl)-1H-pyrazole-5-carboxamide(example I-052)

A mixture of 130 mg (0.47 mmol)1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid,328 mg (0.86 mmol)1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium3-oxid hexafluorophosphate (HATU), 0.17 mL (1.3mmol)N-ethyldiisopropylamine and 2 mL acetonitrile was stirred for 45min at room temperature. 98 mg (0.43 mmol)(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethanaminehydrochloride were added and the mixture stirred over night at roomtemperature. The mixture was then diluted with acetonitrile and adsorbedonto reversed phase silica gel. Purification by reversed phasechromatography (H₂O/acetonitrile) provided 146 mg1-(4-fluorophenyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide.

¹H-NMR (400 MHz, d₆-DMSO): see NMR peak list in table 1

ESI mass [m/z]: 447.2 [M+H]⁺

Synthesis of3-chloro-5-(N-methoxyethanimidoyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamide(example I-057) Step 1:3-acetyl-N-[(2S)-1-amino-1-oxopropan-2-yl]-5-chlorobenzamide

2.494 g (20 mmol) L-alaninamide hydrochloride, 0.994 g (5 mmol) of3-acetyl-5-chlorobenzoic acid (commercially available) and 2.62 mL (15mmol) DIPEA were dissolved in 18.6 mL DMF. 4.4 mL (7.5 mmol) of a T3P®solution (50 wt. % in EtOAc) were added drop wise and the mixture wasstirred over night at room temperature. The solvents were removed underreduced pressure, the remaining residue was taken up with 15 mL waterand 3 mL aqueous saturated NaHCO₃ solution and extracted with 15 mLEtOAc. The aqueous layer was extracted three times more with EtOAc, thecombined organic layers were washed with brine, dried over Na₂SO₄,filtered, and evaporated under reduced pressure to obtain 360 mg (yield:26.7%) of an off-white solid which was used as such in the next step.

¹H-NMR (400 MHz, d₆-DMSO): 8.86-8.85 (d, 1H, NH), 8.38 (s, 1H), 8.21 (s,1H), 8.10 (s, 1H), 7.45 (broad s, 1H, NH₂), 7.02 (broad s, 1H, NH₂),4.45-4.40 (quint., 1H), 2.66 (s, 3H), 1.36-1.34 (d, 3H).

ESI mass [m/z]: 269.2 [M+H]⁺

Step 2:N-[(2S)-1-amino-1-oxopropan-2-yl]-3-chloro-5-(N-methoxyethanimidoyl)benzamide

360 mg (1.34 mmol) of3-acetyl-N-[(2S)-1-amino-1-oxopropan-2-yl]-5-chlorobenzamide, 134 mg(1.60 mmol) methoxyamine hydrochloride and 0.224 mL (1.6 mmol) Et₃N weredissolved in 15 mL acetonitrile and refluxed for 48 h. The solvents wereremoved under reduced pressure, the remaining residue was taken up withdichloromethane and washed with water. The aqueous phase was extractedthree times with dichloromethane, the combined organic layers were driedover Na₂SO₄, filtered, and evaporated under reduced pressure to obtain304 mg (yield: 70.8%) of an off-white solid which was used as such inthe next step.

¹H-NMR (400 MHz, d₆-DMSO): 8.73-8.71 (d, 1H, NH), 8.08 (s, 1H), 7.99 (s,1H), 7.84 (s, 1H), 7.42 (broad s, 1H, NH₂), 7.00 (broad s, 1H, NH₂),4.44-4.39 (quint., 1H), 3.32 (s, 3H), 2.21 (s, 3H), 1.34-1.32 (d, 3H).

ESI mass [m/z]: 298.1 [M+H]⁺

Step 3:3-chloro-5-(N-methoxyethanimidoyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamide(example I-057)

304 mg (1.02 mmol) ofN-[(2S)-1-amino-1-oxopropan-2-yl]-3-chloro-5-(N-methoxyethanimidoyl)benzamideand 182 mg (1.53 mmol) N,N-dimethylformamide dimethyl acetal weredissolved in 20 mL dichloromethane and refluxed for 2 h. The solventswere removed under reduced pressure, the remaining residue was taken upwith a mixture of 10 mL dioxane and 1 mL HOAc. 137 mg (1.24 mmol) of2-hydrazinopyrimidine were added and the reaction mixture was stirred at50° C. over night. After evaporation of the solvents under reducedpressure, the residue was dissolved in dichloromethane, washed with anaqueous saturated NaHCO₃ solution, and the separated organic phase wasreduced in vacuo again. Purification by reversed phase chromatography(H₂O/acetonitrile) provided 148 mg (yield: 35.2%) of the title compoundas an off-white solid.

¹H-NMR (400 MHz, d₆-DMSO): see NMR peaklist in table 1.

ESI mass [m/z]: 400.2 [M+H]⁺

Synthesis of3-chloro-N-{(1R)-1-[1-(5-cyanopyridin-2-yl)-1H-1,2,4-triazol-5-yl]-2-methoxyethyl}-5-(methylsulfonyl)benzamide(example I-058) Step 1:N-[3-chloro-5-(methylsulfonyl)benzoyl]-O-methyl-L-serine

1 g (8.39 mmol) of O-methyl-L-serine and 3.22 mL (18.4 mmol) DIPEA weredissolved in 50 mL dichloromethane. To this reaction mixture, 2.23 g(8.81 mmol) of 3-chloro-5-(methylsulfonyl)benzoyl chloride dissolved in20 mL dichloromethane were added drop wise. The reaction mixture wasstirred at room temperature over night, followed by work-up with water.The aqueous phase was extracted three times with dichloromethane, thecombined organic layers were dried over Na₂SO₄, filtered and evaporatedunder reduced pressure. 622 mg of the title compound were obtained afterpurification via pHPLC and were used as such in the next step.

ESI mass [m/z]: 334.0 [M+H]⁺

Step 2:N-[(2S)-1-amino-3-methoxy-1-oxopropan-2-yl]-3-chloro-5-(methylsulfonyl)benzamide

622 mg (1.85 mmol) ofN-[3-chloro-5-(methylsulfonyl)benzoyl]-O-methyl-L-serine were dissolvedin 18.6 mL THF. 0.24 mL (1.85 mmol) isobutylchloroformate andsubsequently 0.204 mL (1.85 mmol)N-methyl morpholine were added dropwise at −15° C. and the mixture was stirred at −15° C. for 15 min. 0.42mL (2.68 mmol) ammonia (25% wt % in water) were added drop wise at −15°C. The temperature was kept for 45 min, followed by quenching with brineat room temperature. The reaction mixture was extracted with EtOAc threetimes, the combined organic layers were dried over Na₂SO₄, filtered andevaporated under reduced pressure. 473 mg of the title compound wereobtained and used as such in the next step.

ESI mass [m/z]: 335.1 [M+H]⁺

Step 3:3-chloro-N-{(1R)-1-[1-(5-cyanopyridin-2-yl)-1H-1,2,4-triazol-5-yl]-2-methoxyethyl}-5-(methylsulfonyl)benzamide(exampleI-058)

248 mg (0.74 mmol) ofN-[(2S)-1-amino-3-methoxy-1-oxopropan-2-yl]-3-chloro-5-(methylsulfonyl)benzamideand 132 mg (1.11 mmol) N,N-dimethylformamide dimethyl acetal weredissolved in 20 mL dichloromethane and refluxed for 2 h. The solventswere removed under reduced pressure, the remaining residue was taken upwith a mixture of 10 mL dioxane and 1 mL HOAc. 121 mg (0.90 mmol) of6-hydrazinonicotinonitrile were added and the reaction mixture wasstirred at 50° C. over night. After evaporation of the solvents underreduced pressure, the residue was dissolved in dichloromethane, washedwith an aqueous saturated NaHCO₃ solution, and the separated organicphase was reduced in vacuo again. Purification by reversed phasechromatography (H₂O/acetonitrile) provided 77 mg (yield: 19.6%) of thetitle compound.

¹H-NMR (400 MHz, d₆-DMSO): see NMR peaklist in table 1.

ESI mass [m/z]: 461.2 [M+H]⁺

Synthesis of3-chloro-5-[(phenylsulfonyl)amino]-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamide(example I-086) Step 1: methyl3-chloro-5-[(phenylsulfonyl)amino]benzoate

To a solution of 0.52 g (2.83 mmol) methyl 3-amino-5-chlorobenzoate inchloroform (5 mL) at 0° C. were added 1.0 g (5.65 mmol) benzenesulfonylchloride and 0.45 g (5.66 mmol) pyridine and then the reaction mixturewas stirred at room temperature. Once the conversion was complete themixture was poured into a mixture of ice water and a saturated aqueousNH₄Cl solution and extracted with ethyl acetate. The combined organicphases were washed with brine, dried and the solvent was removed underreduced pressure. The remaining residue was chromatographed with acyclohexane/ethyl acetate gradient on silica gel to afford 0.66 g(purity: 99.5%; yield: 71.6%) of the title compound.

ESI mass [m/z]: 326.0 [M+H]⁺

Rt=1.24 min (instrument: LC-MS6)

Step 2: 3-chloro-5-[(phenylsulfonyl)amino]benzoic acid

A solution of 0.66 g (2.03 mmol) methyl3-chloro-5-[(phenylsulfonyl)amino]benzoate in a mixture of 2 mlethanol/THF (1:1) was treated with 8.48 g (8.14 mmol) of a 1 M aqueoussolution of sodium hydroxide. The reaction mixture was stirred 2 hrs atroom temperature. The mixture was poured into a mixture of ice water,ethyl acetate and aqueous HCl 10% solution. The layers were separatedand the aqueous layer was repeatedly extracted with ethyl acetate,washed with water and brine and finally dried. The solvent was removedunder reduced pressure to provide 0.62 g (purity: 97.0%; yield: 94.0%)of the title compound.

ESI mass [m/z]: 312.0 [M+H]⁺

Rt=1.00 min (instrument: LC-MS7)

Step 3:3-chloro-5-[(phenylsulfonyl)amino]-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamide(example I-086)

A solution of 0.21 g (0.66 mmol)3-chloro-5-[(phenylsulfonyl)amino]benzoic acid in 5 dichloromethane wastreated with 0.30 g (0.79 mmol)1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium3-oxid hexafluorophosphate (HATU) and 0.16 ml (0.92 mmol)N,N-diisopropylethylamine and then the mixture was stirred 30 minutes atroom temperature. After that a solution of 0.15 g (0.66 mmol)(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethanaminehydrochloride (1:1) and 0.23 ml (1.32 mmol) N,N-diisopropylethylamine in2.5 ml dichloromethane previously stirred for 30 minutes was added tothe reaction and the mixture was stirred over night at room temperature.The mixture was treated with a saturated aqueous NaH₂PO₄ solution andextracted with dichloromethane. The combined organic layers were driedand finally the volatiles was reduced under pressure. The residue waspurified by reversed phase chromatography (H₂O/acetonitrile) to provide36 mg (purity: 95.5%; yield: 11.0%) of the title compound.

¹H-NMR (400 MHz, d₆-DMSO): see NMR peaklist in table 1.

ESI mass [m/z]: 484.1 [M+H]⁺

Rt=0.97 min (instrument: LC-MS6)

Synthesis of3-chloro-N-{(1S)-1-[1-(2-pyrimidinyl)-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(methylsulfonyl)benzamide(example I-091) Step 1:2-[2-pyrimidinyl]hydrazide-2,2,2-trifluoro-ethanimidic acid

To 1.65 g (15 mmol) 2-hydrazinyl-pyrimidine in methanol (15 mL) 3.87 g(21 mmol) 2,2,2-trifluoro-ethanimidic acid ethyl ester (purity: 76.5%)was added, and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated and the residue was then stirred withn-hexane (30 mL) and ethyl acetate (3 mL). The brownish precipitate wasseparated and dried to obtain 2.6 g (purity: 94.6%; yield: 7.8%)2-[2-pyrimidinyl]hydrazide-2,2,2-trifluoro-ethanimidic acid.

ESI mass [m/z]: 206.0 [M+H]⁺

R_(t)=0.233 min (instrument: LC-MS 7)

Step 2:2-[(1S)-1-[3-(trifluoromethyl)-1-(2-pyrimidinyl)-1H-1,2,4-triazol-5-yl)ethyl]-1H-isoindole-1,3(2H)-dione

To 2.55 g (11.78 mmol)2-[2-pyrimidinyl]hydrazide-2,2,2-trifluoro-ethanimidic acid in pyridine(40 mL), 2.80 g (11.78 mmol)(αS)-1,3-dihydro-α-methyl-1,3-dioxo-2H-isoindole-2-acetyl chloride (seepreparation from(αS)-1,3-dihydro-α-methyl-1,3-dioxo-2H-isoindole-2-acetic acid(Pht-Ala-OH purchased from ABCR) and oxalyl chloride: Tetrahedron:Asymmetry, 21(8), 936-942, 2010) was added, and the reaction mixture wasstirred at room temperature over night. Then water (200 mL) was addedand the mixture was extracted with dichloromethane (200 mL). The organicphase was separated, dried and the solvent was evaporated. The remainingsolid residue was chromatographed with a cyclohexane/acetone gradient onsilica gel to afford 1.65 g (purity: 93.4%; yield: 33.6%) of the titlecompound as a colorless solid.

ESI mass [m/z]: 389.1 [M+H]⁺

R_(t)=1.20 min (instrument: LC-MS 7)

Step 3: (αS)-methyl-1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-methane amine

To 1.6 g (4.12 mmol)2-[(1S)-1-[3-(trifluoromethyl)-1-(1-(2-pyrimidinyl)-1H-1,2,4-triazol-5-yl)ethyl]-1H-isoindole-1,3(2H)-dionein ethanol (40 mL), 937.6 mg (10.30 mmol) hydrazine hydrate was added,and the reaction mixture was heated under reflux. After 30 minutes acolorless precipitate was formed. The reaction mixture was stirred andheated under reflux one additional hour, acetone (20 mL) was added andthe heating was continued for further 30 minutes. The reaction mixturewas concentrated and the solid residue was treated with ethanol. Then,the solvent was evaporated to afford 660 mg (purity: 70%; yield: 43.4%)(αS)-methyl-1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-methane amine, whichwas used for the N-benzoylation reaction (step 4) without purification.

ESI mass [m/z]: 259.0 [M+H]⁺

R_(t)=0.14 min (broad) (instrument: LC-MS 7)

Step 4:3-chloro-N-{(1S)-1-[1-(2-pyrimidinyl)-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(methylsulfonyl)benzamide

To 221.3 mg (0.60 mmol)(αS)-methyl-1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-methane amine, 145.1mg (0.60 mmol) 3-chloro-5-(methylsulfonyl)-benzoic acid, 100.8 mg (0.78mmol) N,N-diisopropylethylamine (Hünig's Base) in N,N-dimethylformamide(DMF) (5 mL), 273.7 mg (0.72 mmol)[O-(7-azabenzotriazol-1-yl)-N,N,N,N′-tetramethyluronium-hexafluorophosphate](HATU) was added, and the reaction mixture was stirred at roomtemperature over night. The reaction mixture was concentrated and thesolid residue was treated with dichloromethane and then extracted with asaturated NaHCO₃ solution and water. The organic phase was separated,dried and the solvent was evaporated. The remaining solid residue waschromatographed with a cyclohexane/acetone gradient on silica gel toafford 100 mg (purity: 98.4%; yield: 34.5%) of the title compound.

¹H-NMR (400 MHz, d₆-DMSO): see NMR peaklist in table 1.

ESI mass [m/z]: 475.0 [M+H]⁺

R_(t)=1.09 min (instrument: LC-MS 7)

Synthesis of3-chloro-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-[(2,2,2-trifluoroethyl)sulfinyl]benzamide(example I-092), and Synthesis of3-chloro-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-[(2,2,2-trifluoroethyl)sulfonyl]benzamide(example I-093) Step 1:3-chloro-5-[(2,2,2-trifluoroethyl)sulfanyl]benzonitrile

To a suspension of 310 mg (7.1 mmol) sodium hydride (55% suspension inmineral oil) in 15 mL anhydrous N,N-dimethylformamide were addedcarefully 0.74 mL (8.35 mmol) 2,2,2-trifluoroethanethiol. After 30 minstirring at room temperature 1.00 g (6.42 mmol)3-chloro-5-fluorobenzonitrile was added. The mixture was stirred for 5hrs at room temperature and then quenched by the addition of 1 mL H₂Oand 1.1 mL glacial acetic acid. The volatiles were removed under reducedpressure. Water and ethyl acetate were added to the residue. The layerswere separated and the aqueous layer repeatedly extracted with ethylacetate. The combined organic layers were washed with brine and thendried with Na₂SO₄. The solvent was removed under reduced pressure andthe residue purified by reversed phase chromatography (H₂O/acetonitrile)to provide 1.40 g of3-chloro-5-[(2,2,2-trifluoroethyl)sulfanyl]benzonitrile.

¹H-NMR (400 MHz, d₆-DMSO): 8.03-8.02 (m, 1H), 7.98-7.97 (m, 1H),7.93-7.92 (m, 1H), 4.30-4.22 (q, 2H).

ESI mass [m/z]: 252.1 [M+H]⁺

Step 2: 3-chloro-5-[(2,2,2-trifluoroethyl)sulfanyl]benzoic acid

A mixture of 800 mg (3.17 mmol)3-chloro-5-[(2,2,2-trifluoroethyl)sulfanyl]benzonitrile, 3.5 mL waterand 3.6 mL concentrated sulfuric acid was heated 2 days at 100° C. Waterand ethyl acetate were added. The layers were separated and the aqueouslayer repeatedly extracted with ethyl acetate. The combined organiclayers were washed with brine and then dried with Na₂SO₄. The solventwas removed under reduced pressure and the residue purified by reversedphase chromatography (H₂O/acetonitrile) to provide 728 mg of3-chloro-5-[(2,2,2-trifluoroethyl)sulfanyl]benzoic acid.

¹H-NMR (400 MHz, d₆-DMSO): 13.55 (s, 1H, COOH), 7.91-7.89 (m, 2H),7.77-7.76 (m, 1H), 4.23-4.16 (q, 2H).

ESI mass [m/z]: 269.0 [M−H]⁻

Step 3:3-chloro-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-[(2,2,2-trifluoroethyl)sulfanyl]benzamide

A mixture of 430 mg (1.58 mmol)3-chloro-5-[(2,2,2-trifluoroethyl)sulfanyl]benzoic acid, 1.05 g (2.77mmol) 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium3-oxid hexafluorophosphate (HATU), 0.53 mL (4.1mmol)N-ethyldiisopropylamine and 5 mL acetonitrile was stirred for 60min at room temperature. 400 mg (90% purity, 1.58 mmol)(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethanaminehydrochloride were added and the mixture stirred over night at roomtemperature. The mixture was then diluted with acetonitrile and adsorbedonto reversed phase silica gel. Purification by reversed phasechromatography (H₂O/acetonitrile) provided 440 mg3-chloro-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-[(2,2,2-trifluoroethyl)sulfanyl]benzamide.

¹H-NMR (400.2 MHz, d₆-DMSO): NMR peak list: δ=9.1997 (1.6); 9.1816(1.6); 8.9905 (10.8); 8.9783 (11.1); 8.1596 (8.2); 7.7896 (1.9); 7.7852(4.2); 7.7807 (2.7); 7.7631 (2.8); 7.7593 (4.4); 7.7553 (2.2); 7.6735(2.8); 7.6692 (3.9); 7.6652 (2.4); 7.6358 (3.0); 7.6236 (5.6); 7.6114(2.8); 5.9856 (1.2); 5.9680 (2.0); 5.9503 (1.2); 5.7569 (0.9); 4.2048(1.1); 4.1791 (3.4); 4.1534 (3.6); 4.1276 (1.2); 3.3240 (13.7); 2.6717(0.4); 2.5254 (1.0); 2.5206 (1.5); 2.5120 (23.4); 2.5074 (48.5); 2.5029(63.6); 2.4982 (44.4); 2.4936 (20.3); 2.3297 (0.4); 1.6339 (7.8); 1.6165(7.7); 1.3975 (16.0); −0.0002 (8.5)

ESI mass [m/z]: 443.1 [M+H]⁺

Step 4:3-chloro-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-[(2,2,2-trifluoroethyl)sulfinyl]benzamide (example I-092) and3-chloro-N-{(1S)-1-[-(pyrimidin-2-yl)-H-1,2,4-triazol-5-yl]ethyl}-5-[(2,2,2-trifluoroethyl)sulfonyl]benzamide(example 1-093)

To a solution of 140 mg (0.31 mmol)3-chloro-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-[(2,2,2-trifluoroethyl)sulfanyl]benzamidein 2 ml CH₂Cl₂ at 0° C. were added 74 mg (70% purity, 0.31 mmol)3-chloroperoxybenzoic acid. The reaction mixture was stirred for 2.5 hrsat 0° C. after which a saturated aqueous NaHCO₃ solution was added. Thelayers were separated and the aqueous layer repeatedly extracted withCH₂Cl₂. The solvent was removed under reduced pressure and the residuepurified by reversed phase chromatography (H₂O/acetonitrile) to provide98 mg of3-chloro-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-[(2,2,2-trifluoroethyl)sulfinyl]benzamide(example I-092) and 38 mg of3-chloro-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-[(2,2,2-trifluoroethyl)sulfonyl]benzamide(example I-093).

Example I-092′H-NMR (400 MHz, d₆-DMSO): see NMR peaklist in table 1.

ESI mass [m/z]: 459.1 [M+H]⁺

Example I-093 ¹H-NMR (400 MHz, d₆-DMSO): see NMR peaklist in table 1.

ESI mass [m/z]: 475.1 [M+H]⁺

Synthesis of3-chloro-5-(1-cyanocyclopropyl)-N-{(1S)-1-[1-(5-cyanopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamide(example I-119) Step 1: methyl 3-chloro-5-(1-cyanocyclopropyl)benzoate

To a solution of methyl 3-chloro-5-(cyanomethyl)benzoate (12 g, 57.24mmol) in 1,2-dibromoethane (150 mL) was added NaOH (4.58 g, 114.49 mmol)and benzyl(trimethyl)ammonium chloride (10.32 g, 68.69 mmol) in oneportion at 25° C. The mixture was stirred at 65° C. for 12 hrs andafterwards diluted with a saturated aqueous solution of NH₄Cl (50 mL)and extracted with EtOAc (50 mL). The aqueous phase was extracted twotimes with EtOAc (30 mL). The combined organic layers were dried overNa₂SO₄ and filtered. The solvent was removed under reduce pressure. Theresidue was purified by column chromatography (silica gel, petrolether/EtOAc=100/1 to 20/1) to give methyl3-chloro-5-(1-cyanocyclopropyl)benzoate (8.8 g, 65% yield) as yellowoil.

Step 2: 3-chloro-5-(1-cyanocyclopropyl)benzoic acid

To a solution of methyl 3-chloro-5-(1-cyanocyclopropyl)benzoate (8.8 g,37.34 mmol) in THF (100 mL) was added TMSOK (6.71 g, 52.28 mmol) in oneportion at 25° C. The mixture was stirred at 25° C. for 12 hrs. Thereaction suspension was adjusted to pH=5 to 6 with 1 M hydrochloricacid. The color of the suspension turned to orange. The mixture wasdiluted with H₂O (15 mL). The water was extracted three times with EtOAc(50 mL). The combined organic layers were dried over Na₂SO₄, filteredand concentrated under reduce pressure to give3-chloro-5-(1-cyanocyclopropyl)benzoic acid (5.05 g, 61% yield) as lightyellow solid.

¹H-NMR (400 MHz, MeOD): δ, 7.85-7.93 (m, 2H), 7.55 (t, J=1.9 Hz, 1H),1.78-1.82 (m, 2H), 1.55-1.59 (m, 2H). Measured using a Varian 400MR NMRmachine.

Step 3:3-chloro-5-(1-cyanocyclopropyl)-N-{(1S)-1-[1-(5-cyanopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamide(example I-119)

A mixture of 116.7 mg (0.52 mmol) 3-chloro-5-(1-cyanocyclopropyl)benzoicacid, 363.1 mg (0.95 mmol)1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium3-oxid hexafluoro-phosphate (HATU), 0.22 mL (1.67mmol)N-ethyldiisopropylamine and 2 mL DMF was stirred for 45 min at roomtemperature. 150 mg (0.47 mmol)6-{5-[(1S)-1-aminoethyl]-1H-1,2,4-triazol-1-yl}nicotinonitrilehydrochloride were added and the mixture stirred over night at roomtemperature. The mixture was then diluted with acetonitrile and adsorbedonto reversed phase silica gel. Purification by reversed phasechromatography (H₂O/acetonitrile) provided 164 mg of the title compoundas colorless solid.

¹H-NMR (400 MHz, d₆-DMSO): see NMR peak list in table 1

ESI mass [m/z]: 418.3 [M+H]⁺

Synthesis ofN-{(1S)-1-[1-(5-cyanopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-cyclopropyl-5-fluorobenzenecarbothioamide(example I-120)

A solution of 70 mg (0.18mmol)N-{(1S)-1-[1-(5-cyanopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-cyclopropyl-5-fluorobenzamidein 2.4 ml toluene was treated with 70 mg (0.18 mmol) Lawesson's reagentand then was stirred at 110° C. for 3 hrs. The reaction mixture wascooled to room temperature and a saturated aqueous NaHCO₃ solution wasadded. The toluene layer was separated and the aqueous phase wasextracted repeatedly with ethyl acetate. The combined organic phaseswere washed with a saturated aqueous NaHCO₃ solution and then dried. Thesolvent was removed under reduced pressure and the residue purified byreversed phase chromatography (H₂O/acetonitrile) to provide 47 mg(purity: 100%; yield: 64.4%) of the title compound.

¹H-NMR (400 MHz, d₆-DMSO): see NMR peaklist in table 1.

ESI mass [m/z]: 393.1 [M+H]⁺

Rt=1.36 min (instrument: LC-MS6)

Synthesis of6-(5-{(1S)-1-[3-chloro-5-(methylsulfonyl)benzamido]ethyl}-1H-1,2,4-triazol-1-yl)-N-cyclopropylnicotinamide(example I-129) Step 1: methyl6-(5-{(1S)-1-[3-chloro-5-(methylsulfonyl)benzamido]ethyl}-1H-1,2,4-triazol-1-yl)nicotinate(example I-122)

1.58 g (5.18mmol)N-[(2S)-1-amino-1-oxopropan-2-yl]-3-chloro-5-(methylsulfonyl)benzamide(intermediate a*-002) was dissolved in 50 mL dichloromethane. 1.03 mL(7.77 mmol) N,N-dimethylformamide dimethylacetal was added and themixture was stirred at 40° C. for 2.5 hrs. Solvents were removed, theremaining residue was dissolved in 50 mL acetic acid, 1.13 g (6.74 mmol)methyl 6-hydrazinonicotinate were added and the mixture was stirred at80° C. for 3 hrs. The volatiles were removed under reduced pressure andthe remaining residue was purified by silica gel chromatography(cyclohexane/EtOAc gradient) to obtain 1.88 g (78%) of example I-122 ascolorless solid.

¹H-NMR (400 MHz, d₆-DMSO): see NMR peaklist in table 1.

ESI mass [m/z]: 464.2 [M+H]⁺

Rt=0.96 min (instrument: LC-MS3)

Step 2:6-(5-{(1S)-1-[3-chloro-5-(methylsulfonyl)benzamido]ethyl}-1H-1,2,4-triazol-1-yl)nicotinicacid (example I-126)

1.78 g (3.83 mmol) methyl6-(5-{(1S)-1-[3-chloro-5-(methylsulfonyl)benzamido]ethyl}-1H-1,2,4-triazol-1-yl)nicotinatewere suspended in 40 mL methanol. 10.7 mL (10.7 mmol) of 1M NaOH wereadded and the mixture was stirred at room temperature over night.Methanol was removed under reduced pressure and the remaining residuewas acidified with 1N HCl to pH 1. The mixture was taken up with EtOAcand the unsoluble solid material was filtered and washed with water andEtOAc and dried under air ventilation to obtain 1.21 g (70%) of exampleI-126 as a colorless solid.

¹H-NMR (400 MHz, d₆-DMSO): see NMR peaklist in table 1.

ESI mass [m/z]: 450.2 [M+H]⁺

Rt=0.74 min (instrument: LC-MS3)

Step 3:6-(5-{(1S)-1-[3-chloro-5-(methylsulfonyl)benzamido]ethyl}-1H-1,2,4-triazol-1-yl)-N-cyclopropylnicotinamide(example I-129)

A mixture of 110 mg (0.24 mmol)6-(5-{(1S)-1-[3-chloro-5-(methylsulfonyl)benzamido]ethyl}-1H-1,2,4-triazol-1-yl)nicotinicacid, 185.4 mg (0.48 mmol)1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium3-oxid hexafluorophosphate (HATU), 0.11 mL (0.85mmol)N-ethyldiisopropylamine and 2 mL DMF was stirred for 60 min at roomtemperature. 0.015 mL (0.22 mmol) cyclopropylamine were added and themixture was stirred over night at room temperature. The mixture was thendiluted with acetonitrile and adsorbed onto reversed phase silica gel.Purification by reversed phase chromatography (H₂O/acetonitrile)provided 48 mg (39%) of the title compound as colorless solid.

¹H-NMR (400 MHz, d₆-DMSO): see NMR peaklist in table 1.

ESI mass [m/z]: 489.3 [M+H]⁺

Rt=0.81 min (instrument: LC-MS3)

Synthesis of3-chloro-N-[(1S)-1-(1-{5-[(cyclopropylcarbonyl)amino]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl}-5-(methylsulfonyl)benzamide(example I-139) Step 1:N—{(S)-1-[1-(5-aminopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-chloro-5-(methylsulfonyl)benzamide (example I-135)

To a solution of 3.0 g (6.7 mmol)3-chloro-5-(methylsulfonyl)-N-{(1S)-1-[1-(5-nitropyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamidein a mixture of 155 mL ethanol and 15 mL acetic acid were added 1.49 g(26.6 mmol) iron powder. The mixture was heated at 80° C. for 1.5 h. Allvolatiles were removed under reduced pressure. Water, ethyl acetate anda saturated aqueous solution of NaHCO₃ were added to the residue. Thelayers were separated and the aqueous layer was extracted several timeswith ethyl acetate. The combined organic layers were washed with brine,dried with Na₂SO₄, filtered and concentrated under reduced pressure togive 2.70 g ofN-{(1S)-1-[1-(5-aminopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-chloro-5-(methylsulfonyl)benzamide.

¹H-NMR (400 MHz, d₆-DMSO): see NMR peaklist in table 1.

ESI mass [m/z]: 421.1 [M+H]⁺

Step 2:3-chloro-N-[(1S)-1-(1-{5-[(cyclopropylcarbonyl)amino]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl]-5-(methylsulfonyl)benzamide(example I-139)

A solution of 150 mg (0.35mmol)N-{(1S)-1-[1-(5-aminopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-chloro-5-(methylsulfonyl)benzamidein 0.6 mL tetrahydrofuran was treated at 0° C. with 37 mg (0.35 mmol)cyclopropanecarbonyl chloride and 0.06 mL (0.4 mmol) triethylamine. Thereaction mixture was stirred over night at room temperature. Water wasadded, the layers separated and the aqueous layer was extracted severaltimes with ethyl acetate. The combined organic layers were washed withbrine, dried with Na₂SO₄, filtered and concentrated under reducedpressure. The residue was purified by reversed phase chromatography(H₂O/acetonitrile) to provide 97 mg of3-chloro-N-[(1S)-1-(1-{5-[(cyclopropylcarbonyl)amino]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl]-5-(methylsulfonyl)benzamide.

¹H-NMR (400 MHz, d₆-DMSO): see NMR peaklist in table 1.

ESI mass [m/z]: 489.1 [M+H]⁺

Analytical Data of the Compounds

The determination of [M+H]⁺ or [M−H]⁻ by LC-MS under acidicchromatographic conditions was done with 1 ml formic acid per literacetonitrile and 0.9 ml formic acid per liter Millipore water aseluents. The column Zorbax Eclipse Plus C18 50 mm*2.1 mm was used. Thetemperature of the column oven was 55° C.

Instruments:

LC-MS3: Waters UPLC with SQD2 mass spectrometer and SampleManagerautosampler. Linear gradient 0.0 to 1.70 minutes from 10% acetonitrileto 95% acetonitrile, from 1.70 to 2.40 minutes constant 95%acetonitrile, flow 0.85 ml/min.

LC-MS6 and LC-MS7: Agilent 1290 LC, Agilent MSD, HTS PAL autosampler.Linear gradient 0.0 to 1.80 minutes from 10% acetonitrile to 95%acetonitrile, from 1.80 to 2.50 minutes constant 95% acetonitrile, flow1.0 ml/min.

The determination of [M+H]⁺ by LC-MS under neutral chromatographicconditions was done with acetonitrile and Millipore water containing 79mg/l ammonia carbonate as eluents.

Instruments:

LC-MS4: Waters IClass Acquity with QDA mass spectrometer and FTNautosampler (column Waters Acquity 1.7 μm 50 mm*2.1 mm, oven temperature45° C.). Linear gradient 0.0 to 2.10 minutes from 10% acetonitrile to95% acetonitrile, from 2.10 to 3.00 minutes constant 95% acetonitrile,flow 0.7 ml/min.

LC-MS5: Agilent 1100 LC system with MSD mass spectrometer and HTS PALautosampler (column: Zorbax XDB C18 1.8 μm 50 mm*4.6 mm, oventemperature 55° C.). Linear gradient 0.0 to 4.25 minutes from 10%acetonitrile to 95% acetonitrile, from 4.25 to 5.80 minutes constant 95%acetonitrile, flow 2.0 ml/min.

The log P values reported in the tables and preparation examples abovewere determined in accordance with EEC directive 79/831 Annex V.A8 byHPLC (High Performance Liquid Chromatography) using a reversed-phasecolumn (C18). Temperature 43° C. The calibration is effected withunbranched alkan-2-ones (having 3 to 16 carbon atoms), for which the logP values are known.

Optical rotations were measured using a Perkin Elmer model 341polarimeter at a wavelength of 589 nm, a pathlength of 10 cm and atemperature of 20° C. They are reported as specific rotations includingthe concentration “c” of the measured compound (in g/100 mL) and thesolvent used.

The determination of the ¹H NMR data was effected with a Bruker AvanceIII 400 Mhz equipped with a 1.7 mm TCI cryo probe, a Bruker Avance III600 Mhz equipped with a 5 mm multi-nuclear cryo probe or a Bruker AvanceNEO 600 Mhz equipped with a 5 mm TCI cryo probe with tetramethylsilaneas reference (0.0) and the solvents CD₃CN, CDCl₃ or D₆-DMSO.

The NMR data of selected examples are listed either in conventional form(6 values, multiplet splitting, number of hydrogen atoms) or as NMR peaklists.

NMR Peak List Method

The ¹H NMR data of selected examples are stated in the form of ¹H NMRpeak lists. For each signal peak, first the 6 value in ppm and then thesignal intensity in round brackets are listed. The pairs of 6value-signal intensity numbers for different signal peaks are listedwith separation from one another by semicolons.

The peak list for one example therefore takes the form of:

δ₁ (intensity₁); δ₂ (intensity₂); . . . ; δ_(i) (intensity_(i)); . . . ;δ_(n) (intensity_(n))

The intensity of sharp signals correlates with the height of the signalsin a printed example of an NMR spectrum in cm and shows the true ratiosof the signal intensities. In the case of broad signals, several peaksor the middle of the signal and the relative intensity thereof may beshown in comparison to the most intense signal in the spectrum.

For calibration of the chemical shift of ¹H NMR spectra, we usetetramethylsilane and/or the chemical shift of the solvent, particularlyin the case of spectra which are measured in DMSO. Therefore, thetetramethylsilane peak may but need not occur in NMR peak lists.

The lists of the ¹H NMR peaks are similar to the conventional ¹H NMRprintouts and thus usually contain all peaks listed in a conventionalNMR interpretation.

In addition, like conventional ¹H NMR printouts, they may show solventsignals, signals of stereoisomers of the target compounds which arelikewise provided by the invention, and/or peaks of impurities.

In the reporting of compound signals within the delta range of solventsand/or water, our lists of ¹H NMR peaks show the standard solvent peaks,for example peaks of DMSO in DMSO-D₆ and the peak of water, whichusually have a high intensity on average.

The peaks of stereoisomers of the target compounds and/or peaks ofimpurities usually have a lower intensity on average than the peaks ofthe target compounds (for example with a purity of >90%).

Such stereoisomers and/or impurities may be typical of the particularpreparation process. Their peaks can thus help in identifyingreproduction of our preparation process with reference to “by-productfingerprints”.

A person skilled in the art calculating the peaks of the targetcompounds by known methods (MestreC, ACD simulation, but also withempirically evaluated expected values) can, if required, isolate thepeaks of the target compounds, optionally using additional intensityfilters. This isolation would be similar to the peak picking in questionin conventional ¹H NMR interpretation.

Further details of ¹H NMR peak lists can be found in the ResearchDisclosure Database Number 564025.

The compounds according to the invention described in table 1 below arelikewise preferred compounds of the formula (I) according to theinvention which are obtained according to or analogously to thepreparation examples described above.

TABLE 1 ESI Exam- mass ple Structure NMR Peaklist¹⁾ [m/z]²⁾ I-001

¹H-NMR (600.1 MHz, CD₃CN, 260K): δ = 8.8882 (3.5); 8.8802 (3.5); 8.8570(0.1); 8.8489 (0.1); 8.5820 (1.1); 8.5741 (1.1); 8.0826 (3.3); 8.0321(1.0); 7.9388 (1.1); 7.9257 (1.2); 7.8312 (0.4); 7.8185 (0.4); 7.7208(0.7); 7.6292 (0.8); 7.6163 (1.7); 7.6033 (0.9); 7.5246 (1.0); 7.5165(1.8); 7.5085 (1.0); 7.5012 (0.3); 7.4882 (0.5); 7.4754 (0.4); 7.4559(0.5); 7.4411 (2.2); 7.4040 (1.3); 7.3913 (1.1); 7.3756 (0.3); 7.3677(0.6); 7.3598 (0.3); 6.3835 (0.3); 6.3720 (1.1); 6.3605 (1.1); 6.3489(0.4); 6.0869 (0.1); 6.0758 (0.4); 6.0644 (0.4); 6.0533 (0.1); 3.6669(0.2); 3.6565 (0.2); 3.6433 (0.3); 3.6329 (0.3); 3.4706 (0.3); 3.4590(0.3); 3.4471 (0.2); 3.4354 (0.2); 3.2626 (0.1); 3.1677 (0.1); 3.1291(0.2); 3.1033 (0.1); 3.0978 (0.1); 3.0542 (16.0); 2.9368 (0.1); 2.8728(0.3); 2.8611 (0.3); 2.8467 (1.1); 2.8349 (1.2); 2.8262 (1.1); 2.8168(1.1); 2.8001 (0.4); 2.7906 (0.3); 2.3022 (11.0); 2.0805 (0.1); 2.0764427.3 (0.1); 2.0723 (0.2); 2.0682 (0.1); 2.0641 (0.1); 1.9856 (0.2);1.9775 (0.4); 1.9696 (9.8); 1.9655 (18.9); 1.9614 (27.6); 1.9573 (19.0);1.9532 (9.6); 1.9445 (0.2); 1.9383 (0.1); 1.8544 (0.1); 1.8504 (0.2);1.8463 (0.2); 1.8420 (0.3); 1.8326 (4.4); 1.8210 (4.5); 1.7774 (1.4);1.7660 (1.4); 1.6565 (0.1); 1.6450 (0.1); 1.2597 (0.1); 1.0283 (0.2);1.0180 (0.2); 1.0077 (0.2); 0.5828 (0.1); 0.5608 (0.4); 0.5512 (0.6);0.5399 (0.5); 0.5184 (0.1); 0.4893 (0.1); 0.4749 (0.2); 0.4673 (0.3);0.4612 (0.3); 0.4515 (0.4); 0.4434 (0.3); 0.4366 (0.3); 0.4293 (0.2);0.4143 (0.1); 0.3269 (0.2); 0.3191 (0.3); 0.3113 (0.3); 0.3056 (0.2);0.2729 (0.2); 0.2641 (0.3); 0.2578 (0.5); 0.2499 (0.7); 0.2430 (0.7);0.2353 (0.5); 0.2287 (0.6); 0.2228 (0.7); 0.2158 (0.8); 0.2095 (0.9);0.2017 (0.7); 0.1956 (0.4); 0.1866 (0.2); 0.0053 (0.1); −0.0001 (2.9);−0.0057 (0.1); −0.2168 (0.2); −0.2250 (0.5); −0.2330 (0.7); −0.2411(0.8); −0.2483 (0.6); −0.2562 (0.2); −0.4070 (0.2); −0.4148 (0.6);−0.4221 (0.8); −0.4301 (0.7); −0.4382 (0.5); −0.4464 (0.2) I-002

¹H-NMR (600.1 MHz, CD₃CN, 260K): δ = 9.2407 (0.1); 9.0845 (2.5); 9.0810(2.8); 9.0158 (0.8); 9.0130 (0.8); 8.8803 (5.1); 8.8722 (5.3); 8.7299(0.9); 8.6226 (1.4); 8.6146 (1.5); 8.6065 (2.8); 8.6036 (3.0); 8.5852(0.1); 8.5816 (0.1); 8.5781 (0.1); 8.1290 (0.8); 8.0950 (4.6); 8.0722(0.1); 8.0472 (1.2); 7.9025 (1.5); 7.8992 (2.8); 7.8960 (1.8); 7.5181(1.4); 7.5100 (2.7); 7.5020 (1.4); 7.4873 (0.1); 7.4134 (0.4); 7.4054(0.7); 7.3974 (0.4); 6.4131 (0.4); 6.4015 (1.5); 6.3899 (1.6); 6.3783(0.5); 6.0705 (0.2); 6.0591 (0.5); 6.0477 (0.5); 6.0363 (0.2); 3.6304(0.3); 3.6196 (0.3); 3.6066 (0.4); 3.5959 (0.4); 3.4970 (0.4); 3.4855(0.4); 3.4734 (0.3); 3.4619 (0.3); 3.2484 (0.1); 3.2396 (0.1); 3.2376(0.1); 3.2012 (0.1); 3.1732 (0.4); 3.1681 (0.2); 3.1483 (0.1); 3.1337(16.0); 3.0158 (0.1); 2.9411 (0.4); 2.9298 (0.4); 2.9148 (1.7); 2.9019(2.4); 2.8912 (1.7); 2.8744 (0.4); 2.8648 (0.4); 2.3187 (0.1); 2.3153428.2 (0.1); 2.2928 (45.2); 2.2601 (0.1); 2.1614 (0.1); 2.0924 (0.2);2.0887 (0.1); 2.0801 (0.2); 2.0760 (0.3); 2.0719 (0.5); 2.0678 (0.3);2.0637 (0.2); 2.0425 (0.1); 2.0113 (0.1); 2.0071 (0.1); 2.0030 (0.1);1.9988 (0.1); 1.9946 (0.1); 1.9852 (1.2); 1.9771 (1.1); 1.9728 (1.8);1.9693 (28.7); 1.9652 (56.0); 1.9610 (82.0); 1.9569 (56.9); 1.9528(28.8); 1.9441 (0.3); 1.9366 (0.1); 1.9339 (0.1); 1.8542 (0.2); 1.8501(0.4); 1.8459 (0.5); 1.8418 (0.4); 1.8306 (6.3); 1.8189 (6.3); 1.7936(0.1); 1.7745 (1.9); 1.7630 (1.8); 1.3630 (0.1); 1.3515 (0.1); 1.2400(0.1); 1.1574 (0.1); 1.1464 (0.1); 0.9749 (0.2); 0.9643 (0.3); 0.9545(0.2); 0.6026 (0.1); 0.5932 (0.2); 0.5891 (0.2); 0.5806 (0.6); 0.5708(0.7); 0.5601 (0.6); 0.5517 (0.3); 0.5473 (0.3); 0.5383 (0.1); 0.5211(0.1); 0.5076 (0.1); 0.4668 (0.1); 0.4526 (0.2); 0.4444 (0.3); 0.4385(0.4); 0.4292 (0.5); 0.4214 (0.4); 0.4142 (0.3); 0.4066 (0.2); 0.3919(0.1); 0.3252 (0.1); 0.3172 (0.3); 0.3089 (0.4); 0.3029 (0.6); 0.2944(0.6); 0.2880 (0.8); 0.2801 (1.0); 0.2722 (0.8); 0.2654 (0.6); 0.2578(0.4); 0.2495 (0.4); 0.2407 (0.7); 0.2335 (0.7); 0.2271 (0.9); 0.2196(0.6); 0.2134 (0.4); 0.2044 (0.2); 0.1758 (0.1); 0.1614 (0.3); 0.1557(0.4); 0.1477 (0.3); 0.1401 (0.2); 0.1319 (0.1); 0.0968 (0.3); 0.0814(0.1); 0.0419 (0.1); 0.0282 (0.1); 0.0227 (0.1); 0.0054 (2.0); −0.0001(60.1); −0.0057 (1.8); −0.1001 (0.2); −0.1984 (0.3) I-003

¹H-NMR (600.1 MHz, CD₃CN, 260K): δ = 8.8859 (4.9); 8.8778 (5.0); 8.6382(1.6); 8.6302 (1.6); 8.0865 (4.4); 8.0335 (1.4); 8.0142 (0.1); 7.9580(2.7); 7.9433 (0.1); 7.9060 (0.1); 7.8124 (1.0); 7.7920 (0.1); 7.6327(1.0); 7.5286 (1.4); 7.5206 (2.6); 7.5125 (1.4); 7.4498 (3.6); 7.4167(0.5); 7.4088 (0.9); 7.4007 (0.5); 7.3889 (2.9); 6.3593 (0.4); 6.3477(1.4); 6.3361 (1.5); 6.3246 (0.5); 6.0860 (0.2); 6.0749 (0.5); 6.0634(0.5); 6.0517 (0.2); 3.8379 (0.3); 3.6910 (0.3); 3.6808 (0.3); 3.6675(0.4); 3.6571 (0.4); 3.5278 (0.4); 3.5160 (0.4); 3.5040 (0.3); 3.4922(0.3); 3.1910 (0.1); 3.1259 (0.4); 3.1151 (0.3); 3.0769 (16.0); 3.0244(0.2); 2.9592 (0.1); 2.9111 (0.6); 2.9037 (0.4); 2.8995 (0.6); 2.8849(1.3); 2.8733 (1.4); 2.8440 (1.3); 2.8345 (1.3); 2.8178 (0.6); 2.8083(0.6); 2.3015 (0.1); 2.2910 (81.9); 2.2744 (0.2); 2.2645 (0.1); 2.2585(0.1); 2.0800 (0.2); 2.0759 (0.4); 2.0718 (0.6); 2.0677 (0.4); 2.0636461.1 (0.2); 1.9851 (1.2); 1.9770 (1.0); 1.9726 (1.7); 1.9692 (37.9);1.9651 (74.7); 1.9609 (110.4); 1.9568 (76.7); 1.9527 (39.4); 1.9440(0.9); 1.9348 (0.4); 1.9307 (0.3); 1.9268 (0.2); 1.9226 (0.2); 1.9182(0.2); 1.9138 (0.2); 1.9096 (0.1); 1.8950 (0.1); 1.8916 (0.1); 1.8873(0.1); 1.8831 (0.1); 1.8789 (0.1); 1.8748 (0.1); 1.8707 (0.1); 1.8622(0.1); 1.8541 (0.3); 1.8500 (0.5); 1.8458 (0.7); 1.8417 (0.5); 1.8376(0.3); 1.8232 (6.0); 1.8116 (6.1); 1.7615 (2.1); 1.7501 (2.1); 1.7134(0.1); 1.7019 (0.1); 1.5085 (0.1); 1.3213 (0.2); 1.3132 (0.2); 1.3096(0.2); 1.3006 (0.2); 1.2879 (0.2); 1.2766 (0.2); 1.2716 (0.2); 1.0585(0.2); 1.0481 (0.3); 1.0378 (0.2); 0.8970 (0.2); 0.8858 (0.5); 0.8738(0.2): 0.5974 (0.1); 0.5877 (0.2); 0.5837 (0.2); 0.5752 (0.5); 0.5643(0.7); 0.5544 (0.6); 0.5418 (0.3); 0.5325 (0.1); 0.5107 (0.1); 0.4954(0.4); 0.4817 (0.6); 0.4741 (0.6); 0.4681 (0.6); 0.4602 (0.4); 0.4523(0.3); 0.4374 (0.1); 0.3496 (0.1); 0.3420 (0.2); 0.3336 (0.3); 0.3259(0.4); 0.3209 (0.3); 0.3083 (0.3); 0.2991 (0.4); 0.2929 (0.7); 0.2851(0.9); 0.2777 (0.8); 0.2702 (0.8); 0.2622 (1.1); 0.2528 (1.0); 0.2459(0.9); 0.2398 (1.0); 0.2322 (0.7); 0.2254 (0.4); 0.2170 (0.2); 0.0967(0.4); 0.0109 (0.2); 0.0054 (2.2); −0.0001 (84.9); −0.0057 (3.1);−0.0124 (1.5); −0.0265 (0.1); −0.0319 (0.1); −0.0376 (0.1); −0.0430(0.1); −0.0580 (0.1); −0.0820 (0.1); −0.1002 (0.4); −0.1791 (0.3);−0.1875 (0.7); −0.1954 (1.0) I-004

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.0075 (1.3); 8.9908 (14.0); 8.9787(14.1); 8.7288 (6.2); 8.7167 (6.3); 8.3166 (0.8); 8.2715 (15.2); 8.2343(5.1); 8.1865 (3.0); 8.1744 (2.9); 8.0920 (0.9); 8.0096 (1.7); 7.9930(2.6); 7.9123 (0.4); 7.6873 (4.6); 7.6751 (8.9); 7.6630 (4.9); 7.6507(0.5); 7.6103 (0.4); 7.5666 (1.2); 7.4133 (0.6); 7.3914 (0.7); 7.3647(0.6); 7.3083 (0.4); 7.2708 (0.5); 7.2647 (0.4); 7.2496 (0.4); 7.2433(0.4); 7.2023 (0.4); 6.6627 (0.3); 6.5048 (1.0); 5.9824 (0.4); 5.9656(1.3); 5.9484 (1.3); 5.9309 (0.4); 5.3358 (0.4); 5.3241 (0.8); 5.3120(0.5); 3.7163 (0.4); 3.6970 (0.5); 3.6593 (1.4); 3.6421 (1.4); 3.6237(0.6); 3.6065 (0.6); 3.3252 (162.0); 2.9782 (1.4); 2.9624 (2.5); 2.9465(2.2); 2.9304 (1.0); 2.9111 (1.3); 2.8004 (2.2); 2.7853 (2.3); 2.7609(1.5); 2.7460 (1.4); 2.6761 (2.0); 2.6715 (3.0); 2.6670 (2.0); 2.6625(1.0); 2.5878 (0.4); 2.5249 (9.5); 2.5114 (167.2); 2.5071 (328.6);2.5026 (427.6); 2.4980 (311.9); 2.4937 (152.6); 2.3384 (0.9); 469.12.3339 (1.9); 2.3294 (2.6); 2.3250 (1.9); 2.1209 (0.4); 2.1052 (0.4);2.0274 (0.9); 2.0089 (1.7); 1.9900 (1.6); 1.9738 (0.7); 1.9576 (0.4);1.7773 (16.0); 1.7598 (16.0); 1.7099 (5.9); 1.6927 (5.8); 1.6255 (0.3);1.6084 (0.4); 1.5705 (0.4); 1.4736 (0.6); 1.4553 (0.7); 1.4419 (0.5);1.3880 (0.7); 1.3820 (1.1); 1.3647 (1.0); 1.3526 (0.7); 1.3451 (0.4);1.3359 (1.6); 1.2984 (9.1); 1.2896 (2.4); 1.2809 (1.9); 1.2589 (13.4);1.2494 (5.6); 1.2353 (13.8); 1.1883 (0.4); 1.1376 (0.3); 1.0984 (0.6);1.0894 (0.6); 1.0723 (0.5); 1.0614 (0.6); 1.0455 (0.4); 1.0331 (0.4);1.0185 (0.4); 0.9247 (0.5); 0.9053 (0.5); 0.8998 (0.4); 0.8878 (0.6);0.8707 (1.5); 0.8541 (3.3); 0.8366 (1.4); 0.6939 (0.4); 0.6769 (0.8);0.4756 (1.6); 0.4600 (1.7); 0.4413 (1.8); 0.4275 (2.7); 0.4175 (2.7);0.4132 (2.9); 0.4081 (2.2); 0.3972 (2.1); 0.3930 (2.0); 0.3830 (0.8);0.3271 (1.4); 0.2464 (0.8); 0.2340 (0.8); 0.2240 (1.8); 0.2122 (2.8);0.2038 (4.1); 0.1937 (3.4); 0.1843 (3.7); 0.1677 (1.8); 0.1574 (2.0);0.1542 (2.0); 0.1456 (1.5); 0.1419 (1.8); 0.1314 (0.4); 0.0079 (0.4);−0.0002 (12.0); −0.0086 (0.4); −0.2736 (0.7); −0.2855 (1.5); −0.2983(1.8); −0.3087 (2.2); −0.4265 (1.6) I-005

¹H-NMR (600.1 MHz, CD₃CN, 260K): δ = 9.0235 (0.2); 9.0154 (0.1); 8.9241(0.4); 8.9161 (0.4); 8.9092 (0.3); 8.9011 (0.4); 8.8879 (0.9); 8.8764(12.2); 8.8684 (12.2); 8.7211 (0.1); 8.7130 (0.1); 8.5912 (0.3); 8.5831(0.5); 8.5723 (2.6); 8.5645 (2.6); 8.4517 (0.1); 8.3799 (0.1); 8.2586(0.1); 8.2337 (0.1); 8.2199 (0.1); 8.1799 (0.2); 8.1638 (0.2); 8.1513(0.1); 8.1383 (0.1); 8.1122 (3.6); 8.0990 (4.0); 8.0877 (11.2); 8.0726(0.8); 8.0596 (0.6); 8.0393 (2.6); 8.0250 (1.0); 8.0122 (1.0); 7.9954(0.1); 7.9814 (0.1); 7.9643 (0.1); 7.9586 (0.1); 7.9462 (0.2); 7.9321(0.2); 7.9115 (1.8); 7.8855 (0.1); 7.8806 (0.1); 7.8713 (0.1); 7.8636(0.1); 7.8547 (0.1); 7.7884 (2.8); 7.7754 (5.8); 7.7623 (3.3); 7.7223(0.6); 7.7106 (1.6); 7.7034 (1.4); 7.6904 (1.3); 7.6755 (4.9); 7.6624(3.7); 7.6295 (6.8); 7.6139 (0.1); 7.5380 (0.2); 7.5276 (0.3); 7.5165(3.4); 7.5084 (6.4); 7.5004 (3.2); 7.4879 (0.2); 7.4743 (0.2); 7.4507481.1 (0.5); 7.4369 (0.4); 7.3810 (0.9); 7.3734 (1.4); 7.3656 (0.7);6.5009 (0.1); 6.4358 (0.1); 6.4239 (0.2); 6.4066 (1.2); 6.3951 (3.8);6.3835 (3.8); 6.3719 (1.2); 6.2934 (0.1); 6.2818 (0.1); 6.1368 (0.1);6.1334 (0.1); 6.0337 (0.3); 6.0227 (0.9); 6.0113 (0.9); 6.0002 (0.3);5.9466 (0.1); 5.9354 (0.1); 5.6189 (0.1); 5.6035 (0.1); 5.4721 (9.8);5.3607 (0.3); 5.3524 (0.5); 5.3443 (0.3); 5.3369 (0.1); 5.3189 (0.1);3.7124 (0.1); 3.6988 (0.1); 3.6872 (0.6); 3.6767 (0.6); 3.6635 (0.7);3.6531 (0.7); 3.5619 (0.1); 3.5496 (0.1); 3.5375 (0.1); 3.4961 (0.7);3.4845 (0.7); 3.4722 (0.6); 3.4607 (0.6); 3.4443 (0.1); 3.4363 (0.1);3.4337 (0.1); 3.4258 (0.1); 3.2372 (0.1); 3.2270 (0.1); 3.2162 (0.1);3.1097 (0.1); 3.0986 (0.1); 3.0329 (0.5); 3.0220 (0.8); 3.0115 (0.5);3.0015 (0.1); 2.9900 (0.2); 2.9792 (0.1); 2.9472 (0.1); 2.9183 (0.3);2.9104 (0.3); 2.8935 (0.1); 2.8817 (0.1); 2.8719 (0.3); 2.8671 (0.3);2.8612 (0.3); 2.8454 (9.0); 2.8349 (9.8); 2.8193 (0.4); 2.8088 (0.1);2.8035 (0.1); 2.7934 (0.1); 2.7793 (0.1); 2.7300 (0.5); 2.6637 (0.6);2.5973 (0.1); 2.3290 (0.1); 2.3232 (0.1); 2.3147 (0.2); 2.2914 (121.5);2.2685 (0.2); 2.2560 (0.3); 2.2479 (0.1); 2.2427 (0.1); 2.1918 (0.1);2.1103 (0.5); 2.0978 (1.0); 2.0851 (0.6); 2.0801 (0.4); 2.0760 (0.7);2.0719 (1.0); 2.0678 (0.7); 2.0637 (0.4); 2.0497 (0.1); 2.0456 (0.1);2.0324 (0.2); 2.0210 (0.6); 2.0114 (0.6); 2.0001 (0.4); 1.9925 (0.2);1.9852 (1.6); 1.9771 (2.6); 1.9692 (61.6); 1.9651 (119.3); 1.9610(175.6); 1.9569 (122.8); 1.9529 (63.2); 1.9354 (0.3); 1.9262 (0.2);1.9229 (0.2); 1.9180 (0.2); 1.8958 (0.1); 1.8917 (0.1); 1.8870 (0.1);1.8830 (0.1); 1.8780 (0.1); 1.8736 (0.1); 1.8687 (0.1); 1.8540 (0.5);1.8501 (0.8); 1.8459 (1.2); 1.8418 (1.1); 1.8292 (15.8); 1.8176 (16.0);1.7871 (0.2); 1.7838 (0.2); 1.7491 (3.9); 1.7377 (3.8); 1.7109 (0.2);1.7000 (0.1); 1.6931 (0.1); 1.6813 (0.1); 1.6756 (0.1); 1.6602 (0.1);1.6408 (0.1); 1.6271 (0.1); 1.6043 (0.1); 1.5882 (0.1); 1.5350 (0.2);1.5249 (0.6); 1.5134 (0.6); 1.5001 (0.3); 1.4780 (0.1); 1.4701 (0.1);1.4580 (0.1); 1.4486 (0.1); 1.4441 (0.1); 1.4279 (0.1); 1.4208 (0.1);1.4108 (0.4); 1.4029 (0.2); 1.3906 (0.2); 1.3771 (0.1); 1.3630 (0.2);1.3517 (0.2); 1.3408 (0.9); 1.3086 (0.8); 1.2826 (2.9); 1.2601 (9.1);1.2169 (0.2); 1.2069 (0.2); 1.1912 (0.4); 1.1758 (0.2); 1.1598 (0.2);1.1519 (0.1); 1.1420 (0.1); 1.1358 (0.1); 1.1246 (0.4); 1.1098 (0.1);1.0974 (0.1); 1.0942 (0.1); 1.0852 (0.5); 1.0737 (1.6); 1.0617 (0.4);1.0506 (0.6); 1.0463 (1.8); 1.0403 (1.6); 1.0294 (1.5); 1.0204 (0.9);0.9820 (0.1); 0.9688 (0.2); 0.9578 (0.2); 0.9493 (0.2); 0.9452 (0.2);0.9372 (0.2); 0.9327 (0.2); 0.9246 (0.3); 0.9168 (0.2); 0.9124 (0.2);0.8927 (1.1); 0.8816 (2.2); 0.8697 (1.2); 0.8528 (0.5); 0.8404 (0.3);0.8151 (0.1); 0.8045 (0.2); 0.7922 (0.1); 0.7816 (0.1); 0.7654 (0.1);0.5550 (0.2); 0.5415 (0.7); 0.5320 (1.6); 0.5225 (2.2); 0.5121 (1.7);0.4997 (0.9); 0.4890 (0.5); 0.4801 (0.6); 0.4641 (1.1); 0.4570 (1.5);0.4434 (1.2); 0.4346 (0.7); 0.4222 (0.2); 0.3916 (0.1); 0.3844 (0.1);0.3712 (0.1); 0.3638 (0.1); 0.3564 (0.1); 0.3392 (0.3); 0.3317 (0.5);0.3236 (0.7); 0.3157 (0.8); 0.2837 (0.1); 0.2734 (0.2); 0.2602 (0.6);0.2515 (1.0); 0.2451 (1.9); 0.2369 (2.6); 0.2299 (2.7); 0.2228 (2.4);0.2150 (2.9); 0.2066 (2.4); 0.1995 (2.3); 0.1932 (2.5); 0.1842 (2.0);0.1721 (1.0); 0.0970 (0.1); 0.0786 (0.2); 0.0243 (0.1); 0.0183 (0.1);0.0054 (0.6); −0.0001 (19.3); −0.1005 (0.1); −0.2529 (0.8); −0.2613(1.9); −0.2693 (2.7); −0.2772 (2.8); −0.2847 (2.1); −0.2926 (0.8);−0.4435 (0.9); −0.4514 (2.2); −0.4590 (2.8); −0.4670 (2.6); −0.4751(1.8); −0.4833 (0.7); I-006

¹H-NMR (600.1 MHz, CD₃CN, 260K): δ = 9.2302 (6.6); 9.2274 (6.7); 9.1826(1.7); 8.9662 (1.9); 8.9087 (0.5); 8.9007 (0.5); 8.8787 (2.9); 8.8703(3.8); 8.8654 (12.4); 8.8574 (12.6); 8.8275 (7.5); 8.8254 (7.6); 8.6277(2.7); 8.6197 (2.8); 8.3294 (1.7); 8.1796 (0.4); 8.1376 (6.8); 8.1175(1.5); 8.1002 (11.3); 8.0520 (2.4); 8.0396 (2.5); 7.5115 (1.0); 7.5064(3.7); 7.4987 (6.7); 7.4907 (3.4); 7.4278 (0.8); 7.4200 (1.4); 7.4122(0.8); 6.5577 (1.0); 6.5466 (1.0); 6.5358 (0.3); 6.4315 (1.2); 6.4199(4.0); 6.4083 (4.0); 6.3967 (1.3); 6.0178 (0.3); 6.0063 (0.9); 5.9951(1.0); 5.9841 (0.3); 5.4718 (1.0); 4.0126 (0.4); 3.6765 (0.4); 3.6651(0.6); 3.6536 (0.5); 3.6472 (0.5); 3.6366 (0.6); 3.6231 (0.8); 3.6129(0.7); 3.5180 (0.7); 3.5065 (0.8); 3.4942 (0.6); 3.4825 (0.5); 2.9753(0.3); 2.9512 (1.3); 2.9391 (0.3); 2.9252 (9.0); 2.9150 (12.1); 2.8985(0.4); 2.6633 (1.4); 2.2933 (196.3); 2.2680 (0.4); 2.2609 (0.4); 2.0791482.1 (0.5); 2.0756 (0.8); 2.0715 (1.2); 2.0675 (0.8); 2.0633 (0.5);1.9848 (1.4); 1.9761 (3.4); 1.9687 (76.1); 1.9647 (147.0); 1.9607(213.5); 1.9566 (152.8); 1.9526 (80.3); 1.9335 (9.5); 1.9155 (0.4);1.8537 (0.6); 1.8496 (1.0); 1.8455 (1.4); 1.8415 (1.2); 1.8287 (15.9);1.8171 (16.0); 1.7445 (3.8); 1.7331 (3.7); 1.6784 (4.3); 1.6674 (4.4);1.5403 (0.5); 1.5286 (0.5); 1.3405 (0.7); 1.3081 (0.3); 1.3040 (0.3);1.2922 (0.4); 1.2823 (1.2); 1.2733 (1.6); 1.2612 (2.9); 1.2321 (7.1);1.2273 (7.1); 1.2208 (7.2); 1.2159 (6.9); 0.9618 (0.7); 0.8808 (0.5);0.8689 (0.3); 0.5943 (0.7); 0.5820 (1.6); 0.5724 (2.2); 0.5622 (1.7);0.5504 (0.8); 0.4540 (0.6); 0.4395 (1.0); 0.4301 (1.0); 0.4160 (0.8);0.4085 (0.6); 0.3218 (0.6); 0.3138 (0.8); 0.3044 (1.4); 0.2961 (1.5);0.2893 (2.1); 0.2814 (2.7); 0.2745 (2.3); 0.2675 (1.7); 0.2589 (1.1);0.2426 (1.1); 0.2338 (1.8); 0.2268 (2.0); 0.2203 (2.5); 0.2126 (1.8);0.2064 (1.1); 0.1975 (0.7); 0.1615 (0.6); 0.1561 (0.8); 0.1481 (0.7);0.1403 (0.5); −0.0004 (2.1) I-007

¹H-NMR (600.1 MHz, CD₃CN, 260K): δ = 8.8814 (10.7); 8.8737 (11.2);8.5786 (6.4); 8.5711 (6.7); 8.0847 (10.6); 8.0271 (6.1); 7.7796 (8.5);7.6351 (4.9); 7.5179 (3.1); 7.5103 (5.7); 7.5026 (3.2); 7.3731 (1.9);7.3656 (3.5); 7.3531 (5.1); 7.2899 (9.2); 7.2422 (4.0); 7.2105 (4.6);7.1805 (8.8); 7.1514 (2.8); 6.3776 (1.3); 6.3662 (3.9); 6.3546 (4.0);6.3433 (1.4); 6.1082 (0.8); 6.0972 (2.3); 6.0859 (2.4); 6.0751 (0.9);5.4727 (6.8); 3.6771 (1.3); 3.6669 (1.4); 3.6537 (1.9); 3.6434 (1.9);3.5426 (1.8); 3.5309 (1.9); 3.5191 (1.4); 3.5074 (1.3); 2.9230 (2.1);2.9113 (2.2); 2.8969 (3.4); 2.8853 (3.4); 2.8126 (5.5); 2.8036 (6.9);2.7937 (4.7); 2.7876 (5.7); 2.7780 (3.7); 2.6208 (0.5); 2.3084 (105.2);2.0981 (0.5); 2.0853 (0.3); 2.0730 (0.6); 2.0198 (0.4); 2.0089 (0.3);1.9851 (0.7); 1.9621 (89.4); 1.9606 (87.8); 1.8468 (0.7); 1.8164 (15.8);1.8049 (16.0); 1.7567 (9.2); 1.7453 (9.0); 1.3067 (0.4); 1.2590 (3.0);1.0581 (1.3); 1.0485 (1.6); 1.0386 (1.3); 0.8916 (0.5); 0.8808 (0.8);0.8691 (0.5); 0.7670 (5.3); 0.7549 (7.2); 0.7443 (9.6); 0.7336 (8.5);0.7093 (0.3); 0.6131 (5.2); 0.5723 (11.3); 0.4723 (2.7); 0.4583 (2.0);0.3441 (1.4); 0.3354 (1.8); 0.3286 (2.1); 466.2 0.2943 (1.0); 0.2710(4.7); 0.2645 (4.7); 0.2578 (3.8); 0.2493 (2.6); 0.2351 (2.6); 0.2283(2.8); 0.2219 (3.0); 0.2142 (2.3); 0.1992 (0.9); 0.1771 (0.3); 0.1647(0.3); 0.1539 (0.4); 0.1472 (0.4); 0.1378 (0.4); 0.1246 (0.5); 0.0968(6.6); 0.0848 (1.0); 0.0656 (0.9); 0.0573 (1.0); 0.0475 (1.2); 0.0364(2.0); −0.0001 (1003.2); −0.1002 (5.6); −0.1764 (0.7); −0.1839 (2.0);−0.1918 (2.8); −0.1995 (3.0); −0.2071 (2.2); −0.3887 (2.4); −0.3963(3.0); −0.4040 (2.8); −0.4118 (1.9); −0.4195 (0.7) I-008

¹H-NMR (600.1 MHz, CD₃CN, 260K): δ = 8.8858 (10.2); 8.8777 (11.8);8.8690 (2.3); 8.6013 (0.7); 8.5932 (0.8); 8.5453 (4.6); 8.5375 (4.7);8.0849 (2.0); 8.0751 (9.2); 8.0299 (0.9); 8.0196 (4.1); 7.9337 (1.2);7.7617 (0.5); 7.5310 (2.9); 7.5230 (5.9); 7.5150 (4.1); 7.4686 (1.3);7.4588 (0.6); 7.4142 (6.4); 7.3991 (0.4); 7.3913 (0.5); 7.3840 (0.3);7.3599 (1.5); 7.3520 (2.5); 7.3444 (1.4); 7.2916 (1.2); 7.1941 (3.4);7.1820 (2.8); 6.9747 (6.4); 6.9224 (2.6); 6.8511 (6.5); 6.3725 (1.2);6.3614 (3.5); 6.3499 (3.5); 6.3386 (1.2); 6.1483 (0.6); 6.1372 (1.7);6.1255 (1.8); 6.1138 (0.8); 6.1027 (0.3); 3.7401 (0.9); 3.7298 (1.0);3.7163 (1.3); 3.7060 (1.3); 3.5349 (1.3); 3.5225 (1.4); 3.5113 (1.0);3.4993 (1.0); 2.9251 (0.3); 2.9136 (0.3); 2.8988 (0.5); 2.8873 (0.5);2.8620 (1.7); 2.8501 (1.7); 2.8358 (2.9); 2.8242 (3.3); 2.7989 (0.4);2.7887 (0.4); 2.7636 (2.7); 2.7541 (2.8); 2.7372 (1.7); 2.7281 (1.6);2.3199 457.2 (0.6); 2.2912 (562.0); 2.2665 (0.7); 2.2584 (0.8); 2.0977(0.4); 2.0798 (1.3); 2.0756 (2.4); 2.0716 (3.5); 2.0675 (2.4); 2.0634(1.3); 2.0071 (0.6); 1.9849 (4.8); 1.9688 (219.6); 1.9648 (416.4);1.9607 (595.7); 1.9567 (418.5); 1.9526 (216.5); 1.9322 (1.7); 1.9170(0.5); 1.9085 (0.4); 1.8984 (0.5); 1.8943 (0.5); 1.8907 (0.5); 1.8866(0.4); 1.8536 (1.5); 1.8497 (2.8); 1.8456 (3.8); 1.8415 (3.2); 1.8375(2.3); 1.8222 (14.5); 1.8108 (16.0); 1.8008 (3.5); 1.7553 (6.8); 1.7439(6.7); 1.5047 (0.3); 1.3084 (0.5); 1.3021 (0.6); 1.2609 (4.0); 1.2424(0.6); 1.0878 (1.2); 1.0772 (1.1); 1.0587 (0.7); 1.0379 (7.1); 1.0268(7.4); 0.9901 (0.4); 0.8938 (0.5); 0.8819 (0.9); 0.8699 (0.5); 0.6964(6.3); 0.6887 (6.3); 0.6710 (1.1); 0.6525 (1.6); 0.6283 (1.4); 0.6100(0.6); 0.5469 (0.5); 0.5253 (2.0); 0.5141 (2.8); 0.5047 (2.9); 0.4933(2.5); 0.4827 (1.8); 0.4760 (1.4); 0.3537 (0.8); 0.3448 (1.2); 0.3377(1.5); 0.3010 (1.6); 0.2933 (1.4); 0.2865 (1.2); 0.2780 (1.4); 0.2699(1.4); 0.2629 (2.0); 0.2549 (2.5); 0.2481 (2.3); 0.2406 (2.0); 0.2337(2.4); 0.2267 (2.2); 0.2189 (2.3); 0.2127 (2.3); 0.2050 (1.6); 0.1900(0.5); −0.0001 (5.8) I-009

¹H-NMR (600.1 MHz, CD₃CN, 260K): δ = 8.9038 (12.6); 8.8958 (12.6);8.8752 (0.3); 8.6657 (7.4); 8.6577 (7.5); 8.6387 (7.2); 8.6307 (7.3);8.0884 (10.0); 8.0811 (6.6); 8.0303 (6.6); 8.0201 (6.4); 7.6627 (5.4);7.6589 (5.6); 7.6387 (3.4); 7.6348 (3.6); 7.5373 (2.0); 7.5306 (4.9);7.5232 (6.6); 7.5154 (3.1); 7.4320 (2.1); 7.4236 (6.9); 7.4159 (2.2);7.4115 (2.3); 7.4033 (3.8); 7.3953 (1.9); 7.3819 (3.9); 7.3781 (3.5);7.2936 (3.6); 7.2897 (3.8); 7.2152 (3.4); 7.2115 (3.5); 7.0104 (0.3);6.9806 (5.6); 6.9768 (5.8); 6.7777 (0.6); 6.7661 (2.0); 6.7544 (2.0);6.7428 (0.6); 6.6507 (3.6); 6.6469 (3.8); 6.3954 (0.9); 6.3840 (2.9);6.3725 (3.0); 6.3611 (1.0); 6.1431 (0.7); 6.1316 (2.2); 6.1201 (2.2);6.1086 (0.7); 5.9389 (0.7); 5.9273 (2.2); 5.9158 (2.2); 5.9042 (0.7);3.8724 (1.2); 3.8618 (1.2); 3.8488 (2.2); 3.8381 (2.1); 3.8285 (2.0);3.8182 (1.9); 3.7746 (3.0); 3.7625 (2.9); 3.7512 (1.8); 3.7391 (1.7);2.9914 453.0 (1.9); 2.9795 (1.9); 2.9652 (2.7); 2.9533 (2.7); 2.8568(0.9); 2.8493 (2.7); 2.8403 (2.6); 2.8307 (2.1); 2.8207 (2.7); 2.8143(2.0); 2.7960 (2.0); 2.7854 (2.0); 2.7698 (0.8); 2.7592 (0.8); 2.2937(173.9); 2.0796 (0.3); 2.0756 (0.7); 2.0715 (1.0); 2.0675 (0.7); 2.0634(0.4); 1.9848 (18.1); 1.9763 (3.6); 1.9687 (58.9); 1.9647 (113.2);1.9606 (164.9); 1.9566 (118.0); 1.9526 (61.8); 1.8538 (0.4); 1.8496(0.7); 1.8456 (1.0); 1.8415 (0.8); 1.8371 (0.6); 1.8265 (8.8); 1.8148(8.8); 1.7955 (13.8); 1.7835 (16.0); 1.7692 (8.9); 1.7547 (0.4); 1.7426(0.4); 1.7284 (8.7); 1.7169 (8.6); 1.2674 (0.5); 1.2590 (1.0); 1.2473(1.1); 1.2360 (0.8); 1.2275 (0.4); 1.1902 (0.6); 1.1793 (0.7); 1.1696(0.4); 1.1607 (0.8); 1.1493 (1.0); 1.1386 (0.8); 1.1301 (0.4); 0.5975(0.3); 0.5921 (0.8); 0.5832 (1.2); 0.5780 (2.1); 0.5703 (1.9); 0.5640(2.4); 0.5567 (1.8); 0.5496 (1.9); 0.5426 (1.6); 0.5358 (1.8); 0.5247(1.5); 0.5192 (1.7); 0.5114 (2.0); 0.5044 (2.6); 0.4954 (2.6); 0.4865(2.1); 0.4791 (1.4); 0.4706 (0.6); 0.4222 (0.6); 0.4146 (1.5); 0.4076(2.0); 0.4001 (2.1); 0.3929 (2.3); 0.3862 (1.7); 0.3786 (0.8); 0.3716(1.0); 0.3642 (1.9); 0.3574 (2.5); 0.3491 (2.3); 0.3436 (2.0); 0.3353(1.6); 0.3234 (0.6); 0.3036 (0.4); 0.2948 (0.6); 0.2883 (1.0); 0.2806(1.3); 0.2735 (1.2); 0.2667 (0.9); 0.2563 (0.9); 0.2477 (1.1); 0.2400(1.2); 0.2335 (1.3); 0.2258 (1.0); 0.2195 (0.5); 0.2109 (0.4); 0.2028(0.4); 0.1876 (1.4); 0.1797 (5.3); 0.1734 (2.2); 0.1663 (5.1); 0.1589(1.3); 0.1438 (0.3); −0.0008 (1.9); −0.1766 (0.4); −0.1845 (1.0);−0.1927 (1.4) I-010

¹H-NMR (600.1 MHz, CD₃CN, 260K): δ = 8.8877 (10.7); 8.8798 (10.9);8.4298 (4.4); 8.4222 (4.4); 8.0879 (9.7); 8.0212 (3.8); 7.9780 (7.1);7.8159 (3.1); 7.6340 (7.5); 7.6213 (9.5); 7.5863 (3.2); 7.5733 (5.1);7.5414 (0.4); 7.5245 (7.1); 7.5118 (16.0); 7.4999 (14.4); 7.4687 (4.8);7.4553 (11.0); 7.4251 (2.7); 7.2610 (7.0); 7.2243 (1.3); 7.2170 (2.3);7.2094 (1.3); 6.4237 (1.2); 6.4123 (3.5); 6.4009 (3.6); 6.3894 (1.2);6.2534 (0.6); 6.2425 (1.6); 6.2312 (1.6); 6.2195 (0.6); 3.7846 (0.9);3.7746 (1.0); 3.7610 (1.2); 3.7508 (1.2); 3.5819 (1.1); 3.5707 (1.2);3.5587 (1.0); 3.5471 (0.9); 2.9461 (1.8); 2.9347 (1.9); 2.9202 (3.0);2.9085 (3.0); 2.8484 (2.9); 2.8391 (3.0); 2.8223 (1.8); 2.8131 (1.8);2.2920 (255.9); 2.2596 (0.5); 2.0758 (1.1); 2.0718 (1.6); 2.0677 (1.2);1.9850 (2.7); 1.9689 (101.5); 1.9650 (197.7); 1.9609 (288.0); 1.9569(211.8); 1.9530 (113.5); 1.9185 (0.3); 1.8533 (14.8); 1.8418 (15.6);1.8102 493.2 (0.4); 1.7813 (6.0); 1.7699 (5.8); 1.2604 (0.4); 1.1201(1.0); 1.1106 (0.8); 0.5842 (1.6); 0.5748 (2.1); 0.5645 (1.8); 0.5416(0.5); 0.5094 (1.9); 0.4952 (1.3); 0.3755 (0.8); 0.3594 (1.4); 0.3235(1.4); 0.2803 (0.7); 0.2653 (1.8); 0.2571 (2.6); 0.2506 (2.5); 0.2414(2.6); 0.2343 (2.6); 0.2257 (2.4); 0.2195 (2.5); 0.2115 (1.7); 0.1965(0.6); −0.0001 (3.0) I-011

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.0428 (5.9); 9.0308 (6.0); 8.8655(9.1); 8.8534 (9.2); 8.2697 (5.6); 8.1855 (8.4); 7.8423 (3.5); 7.8178(4.9); 7.7835 (3.5); 7.6910 (1.7); 7.6790 (3.1); 7.6669 (1.8); 7.6437(3.9); 7.6300 (5.3); 7.5836 (2.6); 7.5715 (4.8); 7.5595 (2.4); 7.5099(5.0); 6.2877 (0.8); 6.2709 (2.9); 6.2535 (3.3); 6.2424 (2.2); 6.2255(1.8); 6.2088 (0.6); 5.7578 (8.2); 4.2199 (1.7); 4.1796 (2.4); 4.0156(2.4); 3.9754 (1.6); 3.7437 (11.4); 3.3265 (31.2); 3.1882 (0.3); 3.1614(4.8); 3.1466 (4.6); 3.1205 (0.3); 3.0457 (0.9); 3.0298 (1.0); 3.0106(1.4); 2.9944 (1.4); 2.9184 (1.4); 2.9017 (1.5); 2.8830 (0.9); 2.8660(0.9); 2.6764 (0.7); 2.6721 (1.0); 2.6678 (0.7); 2.5076 (124.5); 2.5033(158.7); 2.4989 (120.3); 2.3343 (0.8); 2.3300 (1.0); 2.3256 (0.8);1.6206 (16.0); 1.6031 (15.0); 1.2347 (1.3); 0.7482 (1.1); 0.7352 (1.5);0.7221 (1.2); 0.7026 (0.6); 0.4515 (0.4); 0.4374 (0.7); 0.4289 (1.4);465.1 0.4166 (1.9); 0.4068 (2.0); 0.3953 (1.9); 0.3836 (2.3); 0.3713(2.1); 0.3607 (2.3); 0.3504 (2.1); 0.3393 (1.5); 0.3166 (0.5); 0.2063(0.6); 0.1944 (1.3); 0.1826 (1.8); 0.1706 (2.0); 0.1600 (1.4); 0.1470(0.8); 0.0971 (3.1); 0.0769 (2.8); 0.0077 (2.3); −0.0001 (46.9); −0.0081(3.0); −0.0380 (1.8); −0.0503 (2.4); −0.0612 (2.1); −0.0733 (1.9);−0.0852 (1.2); −0.0975 (0.5); −0.4153 (1.1); −0.4279 (1.3); −0.4402(1.0) I-012

¹H-NMR (600.1 MHz, CD₃CN, 260K): δ = 8.8832 (10.1); 8.8751 (10.2);8.4293 (3.7); 8.4214 (3.7); 8.0876 (9.2); 8.0203 (3.3); 7.9481 (5.4);7.7828 (2.4); 7.6550 (3.8); 7.6460 (4.5); 7.6407 (4.8); 7.6317 (4.2);7.6088 (1.6); 7.5953 (2.0); 7.5863 (1.6); 7.5219 (1.9); 7.5040 (2.9);7.4960 (5.4); 7.4879 (2.8); 7.4250 (2.0); 7.4037 (5.5); 7.2771 (5.6);7.2624 (16.0); 7.2479 (5.6); 7.2260 (1.1); 7.2180 (1.9); 7.2100 (1.0);6.4163 (0.9); 6.4047 (3.0); 6.3932 (3.0); 6.3815 (1.0); 6.2197 (1.2);6.2085 (1.2); 3.7857 (0.7); 3.7756 (0.8); 3.7624 (0.9); 3.7520 (0.9);3.5883 (0.9); 3.5767 (1.0); 3.5648 (0.8); 3.5529 (0.7); 3.0550 (0.7);2.9426 (2.1); 2.9303 (1.5); 2.9157 (2.5); 2.9041 (2.5); 2.8458 (2.4);2.8363 (2.5); 2.8196 (1.5); 2.8102 (1.4); 2.2921 (303.8); 2.0802 (0.6);2.0761 (1.1); 2.0720 (1.7); 2.0679 (1.1); 2.0637 (0.6); 1.9929 (0.6);1.9853 (39.7); 1.9771 (3.3); 1.9693 (102.4); 1.9652 (200.4); 1.9611(294.3); 511.1 1.9570 (202.3); 1.9528 (102.3); 1.8793 (0.3); 1.8516(12.5); 1.8460 (4.3); 1.8401 (12.6); 1.7779 (4.8); 1.7664 (4.7); 1.1240(0.8); 0.5728 (1.5); 0.5120 (1.3); 0.3616 (1.0); 0.3288 (1.0); 0.2814(0.5); 0.2664 (1.4); 0.2586 (1.9); 0.2516 (1.8); 0.2426 (1.7); 0.2347(1.8); 0.2260 (1.7); 0.2196 (1.8); 0.2119 (1.3); 0.1969 (0.4); 0.0967(1.4); 0.0054 (9.4); −0.0001 (312.2); −0.0057 (9.8); −0.1002 (1.4);−0.2063 (0.6); −0.2145 (1.4); −0.2225 (2.0); −0.2306 (2.2); −0.2376(1.6); −0.2455 (0.7); −0.3760 (1.6); −0.3831 (2.1); −0.3911 (2.0);−0.3991 (1.3) I-013

¹H-NMR (600.1 MHz, CD₃CN, 260K): δ = 8.9065 (11.2); 8.8986 (16.0);8.8914 (6.3); 8.5721 (5.5); 8.5640 (5.6); 8.5376 (5.2); 8.5295 (5.3);8.0804 (9.9); 8.0705 (5.4); 8.0136 (7.2); 7.5347 (3.0); 7.5266 (5.9);7.5187 (4.1); 7.5117 (3.2); 7.5036 (1.6); 7.4280 (3.2); 7.4146 (5.5);7.3866 (2.3); 7.3743 (3.8); 7.3668 (2.2); 7.3589 (4.0); 7.3508 (2.2);7.3362 (7.1); 7.3254 (7.9); 7.3178 (2.1); 7.3102 (5.4); 7.2976 (4.2);7.2852 (1.9); 7.1556 (0.7); 7.1508 (0.8); 7.1406 (1.2); 7.1266 (2.5);7.1138 (1.7); 7.0328 (1.0); 7.0204 (1.8); 7.0068 (1.0); 6.9343 (3.8);6.9217 (3.5); 6.8892 (2.2); 6.8755 (1.9); 6.7603 (0.6); 6.7494 (2.1);6.7389 (3.4); 6.7265 (1.6); 6.5226 (1.9); 6.5120 (1.7); 6.4923 (1.0);6.4809 (3.0); 6.4694 (3.0); 6.4579 (1.0); 6.0875 (0.5); 6.0760 (1.6);6.0645 (1.6); 6.0530 (0.5); 5.9301 (0.5); 5.9185 (1.6); 5.9069 (1.7);5.8954 (0.6); 5.4713 (9.0); 3.9297 (1.0); 3.9194 (1.0); 3.9058 (1.2);3.8956 383.2 (1.2); 3.8425 (0.8); 3.8324 (0.8); 3.8190 (1.3); 3.8088(1.3); 3.7479 (1.4); 3.7358 (1.4); 3.7244 (0.8); 3.7123 (0.9); 3.7019(1.3); 3.6898 (1.3); 3.6780 (1.0); 3.6660 (1.0); 2.9155 (1.6); 2.9033(1.7); 2.8895 (3.2); 2.8773 (3.2); 2.8384 (2.8); 2.8292 (2.9); 2.8121(1.7); 2.8032 (1.6); 2.7827 (1.9); 2.7717 (1.9); 2.7562 (1.8); 2.7457(1.9); 2.7303 (0.6); 2.7197 (0.7); 2.2968 (182.4); 2.0966 (0.8); 2.0709(1.0); 1.9843 (4.8); 1.9682 (60.9); 1.9642 (117.6); 1.9601 (167.8);1.9560 (118.8); 1.9519 (60.9); 1.8447 (8.7); 1.8330 (7.8); 1.7871(14.1); 1.7755 (14.2); 1.7669 (7.0); 1.7552 (6.8); 1.6991 (6.5); 1.6875(6.4); 1.5127 (0.4); 1.5012 (0.6); 1.2560 (0.7); 1.2441 (0.8); 1.1175(0.7); 0.5783 (0.7); 0.5642 (1.6); 0.5561 (2.0); 0.5480 (2.1); 0.5412(1.8); 0.5339 (1.7); 0.5265 (1.3); 0.5196 (1.2); 0.5123 (1.0); 0.4972(0.9); 0.4885 (1.0); 0.4821 (1.5); 0.4747 (1.8); 0.4672 (1.8); 0.4593(1.2); 0.4058 (1.1); 0.3863 (1.5); 0.3782 (1.4); 0.3716 (0.9); 0.3191(0.9); 0.3125 (1.1); 0.3039 (1.0); 0.2954 (1.1); 0.2870 (1.6); 0.2747(2.4); 0.2661 (2.4); 0.2446 (0.7); 0.2252 (0.5); 0.2028 (1.1); 0.1951(0.8); 0.1437 (0.5); 0.1284 (1.5); 0.1207 (2.0); 0.1130 (1.6); 0.0932(1.1); 0.0844 (1.6); 0.0773 (1.8); 0.0709 (2.0); 0.0632 (1.4); 0.0480(0.5); −0.1926 (0.8); −0.2006 (1.2); −0.2086 (1.2); −0.2166 (0.9);−0.3634 (0.6); −0.3716 (1.5); −0.3792 (2.1); −0.3874 (2.3); −0.3954(1.7); −0.4039 (0.7); −0.4177 (1.0); −0.4255 (1.2); −0.4336 (1.2);−0.4417 (0.8); −0.5275 (0.7); −0.5356 (1.7); −0.5437 (2.2); −0.5517(2.0); −0.5594 (1.4) I-014

¹H-NMR (600.1 MHz, CD₃CN, 260K): δ = 9.1747 (0.3); 9.0532 (0.4); 8.9085(12.1); 8.8997 (14.4); 8.8902 (5.4); 8.6453 (0.9); 8.6251 (7.9); 8.6170(6.9); 8.6048 (5.2); 8.5968 (4.5); 8.3583 (0.4); 8.0886 (9.7); 8.0758(5.6); 8.0304 (6.3); 8.0121 (4.4); 7.9452 (0.8); 7.6020 (0.4); 7.5665(0.6); 7.5359 (4.0); 7.5278 (6.4); 7.5201 (4.0); 7.5152 (3.5); 7.5073(1.7); 7.4706 (0.9); 7.4589 (1.2); 7.4297 (6.4); 7.4156 (8.8); 7.4077(6.3); 7.3929 (2.2); 7.3812 (1.2); 7.3669 (2.9); 7.3523 (4.4); 7.3475(3.6); 7.3381 (8.6); 7.3238 (1.2); 7.2201 (3.8); 7.1252 (1.6); 7.1108(1.6); 7.0628 (2.4); 7.0483 (1.9); 6.9813 (6.3); 6.8770 (2.8); 6.8627(2.4); 6.7724 (0.7); 6.7609 (2.1); 6.7493 (1.9); 6.7373 (0.4); 6.6719(3.9); 6.4326 (1.2); 6.4213 (3.2); 6.4098 (2.9); 6.3981 (0.6); 6.1015(0.7); 6.0899 (1.9); 6.0785 (1.8); 6.0668 (0.4); 6.0001 (0.8); 5.9884(2.4); 5.9771 (2.2); 5.9654 (0.5); 5.4730 (3.7); 5.2414 (0.4); 5.2298417.2 (0.3); 3.8847 (1.4); 3.8743 (1.4); 3.8610 (2.1); 3.8503 (2.9);3.8398 (1.0); 3.8262 (1.6); 3.8160 (1.5); 3.7560 (3.6); 3.7439 (3.6);3.7323 (2.3); 3.7203 (2.2); 3.1342 (0.4); 3.0493 (0.4); 3.0310 (1.2);2.9835 (2.0); 2.9715 (2.0); 2.9574 (2.9); 2.9455 (2.8); 2.8317 (2.8);2.8226 (2.9); 2.8045 (5.5); 2.8000 (5.3); 2.7957 (4.6); 2.7790 (0.3);2.7684 (0.4); 2.7272 (0.5); 2.2962 (181.6); 2.0772 (0.9); 2.0706 (1.2);1.9855 (2.1); 1.9621 (240.1); 1.9614 (238.2); 1.9269 (1.4); 1.8949(0.5); 1.8447 (1.6); 1.830.3 (9.1); 1.8186 (9.2); 1.7889 (15.4); 1.7842(12.2); 1.7776 (16.0); 1.7730 (11.5); 1.7236 (7.4); 1.7121 (7.6); 1.6500(0.5); 1.6378 (0.5); 1.5082 (0.4); 1.4959 (0.4); 1.3843 (1.5); 1.3731(1.4); 1.2614 (1.5); 1.2529 (1.1); 1.2416 (1.2); 1.2305 (0.9); 1.2203(0.3); 1.1922 (1.1); 1.1812 (1.1); 1.1517 (0.6); 1.1412 (0.8); 1.1309(0.6); 0.7992 (0.4); 0.5722 (0.5); 0.5650 (1.2); 0.5577 (1.6); 0.5507(1.7); 0.5429 (1.9); 0.5351 (1.9); 0.5287 (1.8); 0.5199 (1.9); 0.5129(1.4); 0.5049 (1.1); 0.4970 (1.1); 0.4883 (0.9); 0.4857 (0.9); 0.4789(1.1); 0.4706 (1.3); 0.4629 (0.8); 0.4088 (1.0); 0.4014 (1.6); 0.3937(1.7); 0.3871 (1.5); 0.3803 (0.8); 0.3534 (1.8); 0.3476 (1.9); 0.3410(2.1); 0.3319 (1.3); 0.1677 (3.1); 0.1546 (2.4); 0.0969 (3.9); −0.0001(1442.4); −0.0846 (6.1); −0.1002 (12.9); −0.1673 (3.1); −0.1759 (3.7);−0.1839 (4.1); −0.1920 (4.1); −0.1998 (3.7); −0.2076 (2.9); −0.2181(2.4); −0.2262 (2.6); −0.2346 (2.6); −0.2423 (2.5); −0.2493 (2.3);−0.3160 (1.6); −0.3250 (1.6); −0.3355 (2.8); −0.3441 (3.5); −0.3517(3.5); −0.3590 (3.5); −0.3658 (2.3); −0.4207 (1.5); −0.4297 (2.8);−0.4374 (4.5); −0.4449 (4.7); −0.4529 (4.6); −0.4612 (3.3); −0.5414(1.1); −0.5530 (1.0); −0.6287 (0.9); −0.6476 (0.9); −0.6545 (0.8);−0.6638 (0.8); −0.6729 (0.8); −0.6894 (0.8); −0.6993 (0.8); −0.7397(0.8); −0.7964 (0.7); −0.8304 (0.7); −0.8391 (0.6); −0.8801 (0.6);−0.8904 (0.6); −0.8992 (0.6); −0.9293 (0.6); −0.9403 (0.6); −0.9439(0.6); −0.9494 (0.6); −0.9705 (0.6); −0.9857 (0.6); −1.0010 (0.5);−1.0205 (0.5); −1.0447 (0.5); −1.0512 (0.5); −1.0744 (0.5); −1.0958(0.5); −1.1334 (0.5); −1.2053 (0.4); −1.2109 (0.4); −1.2264 (0.4);−1.2555 (0.4); −1.2604 (0.4); −1.2733 (0.4); −1.2883 (0.4); −1.3039(0.4); −1.3260 (0.4); −1.3466 (0.4); −1.3590 (0.4); −1.3772 (0.4);−1.4025 (0.4); −1.4265 (0.3); −1.4391 (0.3); −1.4498 (0.3); −1.4562(0.3); −1.4632 (0.3); −1.4780 (0.3) I-015

¹H-NMR (600.1 MHz, CD₃CN, 260K): δ = 8.9069 (4.4); 8.8986 (12.1); 8.8906(8.2); 8.6411 (5.2); 8.6330 (5.2); 8.6101 (5.5); 8.6021 (5.6); 8.0852(7.3); 8.0204 (7.9); 7.9431 (0.9); 7.5353 (3.3); 7.5293 (3.9); 7.5213(7.9); 7.5060 (3.4); 7.4999 (4.3); 7.4860 (4.1); 7.4385 (1.4); 7.4305(2.7); 7.4225 (1.4); 7.4157 (1.6); 7.4077 (3.0); 7.3997 (1.5); 7.3159(3.2); 7.3021 (2.7); 7.1302 (2.2); 7.1162 (2.1); 6.9476 (2.6); 6.9339(2.8); 6.9261 (4.1); 6.9122 (3.9); 6.7829 (0.5); 6.7715 (1.4); 6.7598(1.4); 6.7484 (0.5); 6.4923 (2.7); 6.4786 (2.6); 6.4418 (0.8); 6.4305(2.4); 6.4190 (2.4); 6.4075 (0.8); 6.1560 (0.6); 6.1447 (1.9); 6.1331(2.0); 6.1218 (0.6); 5.9185 (0.5); 5.9072 (1.7); 5.8956 (1.7); 5.8840(0.6); 5.4723 (4.8); 5.2388 (0.4); 5.2272 (0.4); 3.8922 (1.0); 3.8816(1.0); 3.8681 (1.4); 3.8580 (1.6); 3.8522 (1.0); 3.8386 (1.7); 3.8283(1.7); 3.7821 (1.7); 3.7700 (1.8); 3.7534 (1.5); 3.7416 (1.5); 3.7293453.0 (1.0); 3.7174 (1.0); 3.1854 (0.3); 3.0327 (1.0); 2.9483 (1.3);2.9363 (1.3); 2.9222 (2.3); 2.9102 (2.3); 2.8525 (2.2); 2.8434 (2.2);2.8268 (1.8); 2.8171 (1.9); 2.8017 (1.4); 2.7898 (2.2); 2.7560 (1.3);2.7454 (1.4); 2.7295 (0.7); 2.7194 (0.8); 2.6929 (0.7); 2.2961 (162.5);2.2802 (0.9); 2.2693 (0.6); 2.0976 (1.0); 2.0854 (0.8); 2.0751 (1.0);2.0649 (0.8); 2.0206 (0.3); 2.0108 (0.4); 1.9851 (1.0); 1.9618 (141.4);1.9603 (138.5); 1.8447 (1.0); 1.8350 (6.1); 1.8232 (6.0); 1.7856 (16.0);1.7741 (15.8); 1.7263 (7.4); 1.7147 (7.4); 1.3832 (1.6); 1.3719 (1.6);1.2604 (2.9); 1.2453 (1.0); 1.2352 (0.5); 1.1913 (1.9); 1.1804 (2.2);1.1696 (0.8); 1.1594 (0.4); 0.8925 (0.4); 0.8818 (0.8); 0.8701 (0.4);0.5972 (0.6); 0.5892 (1.0); 0.5823 (1.6); 0.5750 (1.9); 0.5679 (2.1);0.5603 (2.0); 0.5530 (2.5); 0.5387 (1.7); 0.5358 (1.7); 0.5326 (1.8);0.5141 (1.7); 0.5085 (1.4); 0.4998 (1.6); 0.4926 (1.6); 0.4846 (1.2);0.4771 (0.4); 0.4179 (1.6); 0.4093 (1.9); 0.3974 (3.3); 0.3711 (0.6);0.3596 (0.5); 0.3509 (0.4); 0.3438 (0.4); 0.2896 (1.1); 0.2802 (1.7);0.2679 (1.9); 0.2586 (1.4); 0.2481 (1.0); 0.2428 (1.0); 0.2342 (1.1);0.2264 (1.2); 0.2183 (1.0); 0.2114 (0.8); 0.2036 (0.6); 0.1594 (0.4);0.1507 (0.6); 0.1441 (1.1); 0.1357 (1.6); 0.1294 (1.5); 0.1209 (1.8);0.1134 (1.9); 0.1049 (1.6); 0.0970 (9.4); 0.0784 (0.9); 0.0461 (0.7);0.0375 (0.8); −0.0001 (1384.6); −0.0277 (1.2); −0.0345 (1.1); −0.0422(1.0); −0.0507 (1.1); −0.0571 (0.9); −0.0655 (1.0); −0.0844 (0.9);−0.1000 (8.2); −0.1669 (0.4); −0.1747 (0.8); −0.1826 (1.0); −0.1904(1.1); −0.1983 (0.8); −0.2065 (0.4); −0.2281 (0.4); −0.2361 (0.6);−0.2440 (0.5); −0.2515 (0.4); −0.3189 (0.5); −0.3267 (1.2); −0.3340(1.8); −0.3419 (1.9); −0.3502 (1.5); −0.3584 (0.6); −0.3746 (0.3);−0.3829 (0.8); −0.3909 (1.1); −0.3987 (1.0); −0.4069 (0.7); −0.4630(0.6); −0.4709 (1.4); −0.4791 (1.8); −0.4868 (1.6); −0.4942 (1.1);−0.5016 (0.4) I-016

¹H-NMR (600.1 MHz, CD₃CN, 260K): δ = 8.9118 (7.5); 8.9047 (16.0); 8.8968(13.6); 8.6157 (7.1); 8.6076 (7.2); 8.5720 (8.4); 8.5639 (8.5); 8.0839(11.5); 8.0785 (6.2); 8.0249 (6.5); 8.0126 (5.6); 7.5629 (3.4); 7.5606(3.5); 7.5495 (3.9); 7.5471 (3.8); 7.5441 (2.0); 7.5417 (2.0); 7.5387(2.2); 7.5341 (3.9); 7.5306 (6.2); 7.5279 (3.1); 7.5261 (7.4); 7.5226(2.2); 7.5180 (3.6); 7.3879 (2.3); 7.3838 (2.1); 7.3798 (4.6); 7.3757(3.9); 7.3717 (2.4); 7.3676 (2.0); 7.3534 (0.6); 7.3505 (0.6); 7.3441(0.4); 7.3401 (0.5); 7.3371 (1.0); 7.3323 (2.6); 7.3265 (5.8); 7.3215(7.2); 7.3191 (8.6); 7.3127 (2.4); 7.3084 (0.9); 7.3048 (5.0); 7.2916(5.9); 7.2785 (3.4); 7.1801 (1.9); 7.1777 (1.9); 7.1667 (2.0); 7.1643(2.0); 7.1039 (1.9); 7.1015 (1.9); 7.0911 (1.7); 7.0888 (1.7); 6.9167(3.5); 6.9143 (3.6); 6.9040 (3.4); 6.9016 (3.3); 6.7718 (0.5); 6.7601(1.7); 6.7564 (2.0); 6.7484 (1.7); 6.7435 (3.3); 6.7368 (0.5); 6.7304417.1 (1.9); 6.4872 (2.0); 6.4848 (2.0); 6.4746 (1.9); 6.4722 (1.8);6.4596 (0.8); 6.4481 (2.5); 6.4366 (2.5); 6.4251 (0.8); 6.1523 (0.6);6.1407 (2.0); 6.1292 (2.0); 6.1176 (0.6); 5.9033 (0.5); 5.8917 (1.7);5.8801 (1.7); 5.8684 (0.5); 5.4725 (1.4); 3.9193 (1.0); 3.9088 (1.0);3.8954 (1.3); 3.8849 (1.3); 3.8490 (1.0); 3.8388 (1.0); 3.8255 (1.7);3.8152 (1.7); 3.7699 (1.9); 3.7577 (1.9); 3.7463 (1.1); 3.7341 (1.1);3.7276 (1.4); 3.7156 (1.4); 3.7037 (1.1); 3.6918 (1.1); 2.9273 (1.6);2.9151 (1.6); 2.9012 (3.0); 2.8890 (3.0); 2.8501 (2.5); 2.8409 (2.5);2.8309 (0.9); 2.8239 (1.4); 2.8201 (1.0); 2.8148 (1.3); 2.8048 (1.5);2.7940 (1.5); 2.7482 (1.5); 2.7376 (1.5); 2.7221 (0.8); 2.7115 (0.8);2.2927 (45.4); 2.0763 (0.5); 2.0722 (0.8); 2.0681 (0.5); 1.9855 (0.4);1.9774 (1.5); 1.9696 (45.7); 1.9654 (89.0); 1.9613 (130.4); 1.9572(89.2); 1.9531 (44.9); 1.9487 (1.2); 1.9444 (0.4); 1.8503 (0.6); 1.8462(1.0); 1.8413 (8.2); 1.8295 (7.9); 1.7935 (13.9); 1.7820 (13.8); 1.7672(7.1); 1.7556 (7.1); 1.7079 (8.5); 1.6963 (8.5); 1.2671 (0.5); 1.2641(0.4); 1.2620 (0.4); 1.2561 (0.7); 1.2474 (0.4); 1.2448 (0.5); 1.1941(0.6); 1.1831 (0.6); 1.1444 (0.6); 1.1404 (0.4); 1.1340 (0.7); 1.1323(0.7); 1.1264 (0.4); 1.1221 (0.6); 0.5931 (0.5); 0.5870 (0.6); 0.5839(0.7); 0.5792 (1.5); 0.5735 (1.2); 0.5709 (1.1); 0.5651 (1.6); 0.5594(0.8); 0.5575 (0.8); 0.5509 (0.8); 0.5470 (0.6); 0.5445 (0.7); 0.5385(1.0); 0.5362 (0.9); 0.5317 (1.2); 0.5233 (1.5); 0.5191 (1.0); 0.5158(0.9); 0.5093 (1.7); 0.5021 (1.3); 0.5008 (1.3); 0.4944 (1.7); 0.4870(1.8); 0.4802 (1.6); 0.4719 (0.6); 0.4651 (0.4); 0.4228 (0.5); 0.4145(0.9); 0.4087 (0.9); 0.4057 (1.0); 0.4021 (1.1); 0.3954 (1.4); 0.3870(1.5); 0.3808 (1.0); 0.3725 (0.5); 0.3431 (0.5); 0.3345 (1.0); 0.3283(1.2); 0.3196 (1.0); 0.3128 (0.6); 0.3041 (0.3); 0.2986 (0.4); 0.2925(0.6); 0.2903 (0.5); 0.2853 (1.3); 0.2821 (0.9); 0.2769 (1.8); 0.2721(1.4); 0.2695 (1.5); 0.2637 (1.6); 0.2606 (1.2); 0.2561 (1.0); 0.2509(0.6); 0.2471 (0.7); 0.2359 (0.5); 0.2285 (0.6); 0.2268 (0.6); 0.2222(0.6); 0.2196 (0.6); 0.2134 (0.9); 0.2058 (0.6); 0.2000 (0.3); 0.1982(0.3); 0.1533 (0.4); 0.1458 (0.5); 0.1441 (0.6); 0.1380 (1.2); 0.1307(1.5); 0.1240 (1.2); 0.1223 (1.2); 0.1173 (0.9); 0.1154 (0.9); 0.1075(1.5); 0.1001 (1.2); 0.0981 (1.3); 0.0936 (1.2); 0.0913 (1.4); 0.0849(1.6); 0.0775 (1.2); 0.0715 (0.6); 0.0696 (0.5); 0.0622 (0.5); 0.0054(4.2); −0.0001 (138.3); −0.0057 (4.0); −0.1002 (0.6); −0.2120 (0.7);−0.2200 (1.0); −0.2283 (1.1); −0.2358 (0.8); −0.2442 (0.4); −0.3370(0.6); −0.3453 (1.2); −0.3524 (1.9); −0.3608 (1.9); −0.3689 (1.4);−0.3772 (0.7); −0.3850 (0.4); −0.3933 (0.8); −0.4009 (1.0); −0.4093(1.0); −0.4173 (0.6); −0.4948 (0.6); −0.5029 (1.3); −0.5111 (1.8);−0.5192 (1.6); −0.5264 (1.1); −0.5347 (0.4) I-017

¹H-NMR (600.1 MHz, CD₃CN, 260K): δ = 8.8963 (14.2); 8.8937 (9.4); 8.8882(14.6); 8.8856 (9.4); 8.6457 (10.4); 8.6376 (10.7); 8.6170 (8.9); 8.6090(9.1); 8.0833 (11.8); 8.0744 (6.4); 8.0179 (8.4); 8.0133 (7.2); 7.5340(6.4); 7.5308 (6.9); 7.5277 (4.3); 7.5195 (7.4); 7.5114 (4.2); 7.5093(4.6); 7.5011 (2.0); 7.4512 (2.6); 7.4473 (3.6); 7.4433 (7.5); 7.4351(2.5); 7.4314 (3.0); 7.4233 (5.6); 7.4152 (2.9); 7.4106 (5.1); 7.4073(5.2); 7.3976 (0.4); 7.3765 (1.9); 7.3733 (1.8); 7.3628 (2.2); 7.3595(2.1); 7.3426 (3.6); 7.3393 (3.7); 7.3317 (11.6); 7.3256 (4.1); 7.1689(3.5); 7.1551 (3.1); 6.9598 (6.6); 6.9459 (9.2); 6.7822 (0.6); 6.7706(1.9); 6.7651 (2.9); 6.7618 (3.2); 6.7592 (2.2); 6.7515 (3.1); 6.7482(3.6); 6.5381 (5.3); 6.5244 (4.7); 6.4641 (0.9); 6.4526 (3.1); 6.4411(3.1); 6.4296 (1.0); 6.0843 (0.7); 6.0728 (2.2); 6.0612 (2.3); 6.0496(0.7); 5.9413 (0.8); 5.9297 (2.6); 5.9180 (2.6); 5.9064 (0.8); 5.4724417.1 (6.3); 3.8983 (1.5); 3.8879 (1.6); 3.8745 (2.1); 3.8641 (2.1);3.8524 (1.1); 3.8422 (1.2); 3.8289 (1.9); 3.8185 (1.9); 3.7612 (2.0);3.7491 (2.0); 3.7376 (1.3); 3.7330 (2.2); 3.7255 (1.4); 3.7210 (2.3);3.7092 (1.7); 3.6971 (1.7); 2.9332 (1.9); 2.9210 (1.9); 2.9071 (3.2);2.8949 (3.2); 2.8378 (2.8); 2.8286 (2.9); 2.8163 (0.9); 2.8118 (1.8);2.8027 (1.8); 2.7904 (2.0); 2.7794 (2.0); 2.7604 (1.9); 2.7499 (1.9);2.7344 (0.7); 2.7239 (0.7); 2.2918 (51.8); 2.0803 (0.4); 2.0762 (0.7);2.0721 (1.1); 2.0680 (0.7); 2.0639 (0.4); 1.9855 (3.4); 1.9813 (0.3);1.9773 (1.8); 1.9695 (64.1); 1.9654 (125.8); 1.9613 (185.1); 1.9571(127.6); 1.9530 (64.8); 1.9443 (1.1); 1.9404 (0.5); 1.9356 (0.3); 1.8544(0.4); 1.8503 (0.7); 1.8462 (1.1); 1.8421 (0.9); 1.8379 (0.5); 1.8292(8.5); 1.8175 (8.5); 1.7841 (11.4); 1.7778 (16.0); 1.7725 (12.3); 1.7663(15.6); 1.7201 (9.3); 1.7085 (9.3); 1.3193 (0.3); 1.3083 (0.4); 1.3022(0.4); 1.2913 (0.4); 1.2648 (0.5); 1.2565 (0.9); 1.2447 (1.0); 1.2339(0.8); 1.2252 (0.4); 1.2206 (0.3); 1.1894 (0.8); 1.1851 (0.4); 1.1782(1.2); 1.1649 (0.9); 1.1585 (0.6); 1.1543 (0.7); 0.5887 (0.4); 0.5831(1.0); 0.5766 (1.1); 0.5739 (1.1); 0.5690 (1.8); 0.5646 (1.7); 0.5598(2.0); 0.5556 (1.7); 0.5511 (2.4); 0.5437 (2.5); 0.5367 (2.6); 0.5306(1.6); 0.5278 (1.6); 0.5229 (2.5); 0.5175 (1.5); 0.5126 (1.4); 0.5095(1.5); 0.5034 (1.5); 0.4964 (1.3); 0.4909 (1.1); 0.4882 (1.5); 0.4822(1.9); 0.4735 (1.7); 0.4667 (1.3); 0.4580 (0.6); 0.4182 (0.7); 0.4097(1.6); 0.4035 (1.6); 0.4017 (1.6); 0.3976 (1.4); 0.3938 (2.0); 0.3897(2.0); 0.3848 (2.2); 0.3808 (1.8); 0.3779 (1.7); 0.3726 (1.4); 0.3694(1.0); 0.3645 (0.8); 0.3566 (0.5); 0.3082 (0.4); 0.3004 (0.8); 0.2945(1.5); 0.2914 (1.3); 0.2861 (2.2); 0.2828 (1.8); 0.2780 (2.1); 0.2730(1.9); 0.2698 (1.6); 0.2649 (1.2); 0.2556 (0.6); 0.2342 (0.7); 0.2250(0.8); 0.2174 (0.8); 0.2112 (1.1); 0.2034 (0.8); 0.1975 (0.4); 0.1614(0.5); 0.1526 (0.7); 0.1465 (1.4); 0.1387 (1.9); 0.1315 (1.9); 0.1235(2.4); 0.1170 (2.4); 0.1084 (1.8); 0.1019 (1.9); 0.0947 (1.5); 0.0867(0.6); 0.0793 (0.5); 0.0054 (5.8); −0.0001 (189.6); −0.0057 (5.9);−0.1002 (0.8); −0.1724 (0.4); −0.1806 (0.8); −0.1886 (1.2); −0.1968(1.3); −0.2047 (0.9); −0.2130 (0.4); −0.3337 (0.6); −0.3417 (1.5);−0.3484 (2.2); −0.3567 (2.4); −0.3648 (1.7); −0.3731 (0.8); −0.4086(0.4); −0.4170 (1.0); −0.4250 (1.2); −0.4330 (1.2); −0.4412 (0.8);−0.4495 (0.4); −0.4889 (0.7); −0.4970 (1.7); −0.5052 (2.2); −0.5132(2.0); −0.5200 (1.3); −0.5280 (0.5) I-018

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 8.9632 (13.2); 8.9511 (13.5); 8.7285(6.0); 8.7163 (6.1); 8.2657 (12.3); 8.2409 (5.0); 7.6591 (3.7); 7.6470(7.2); 7.6348 (3.6); 7.5636 (1.6); 7.5514 (3.1); 7.5392 (1.6); 7.5326(0.7); 7.5155 (1.4); 7.5114 (1.5); 7.4945 (2.7); 7.4775 (1.6); 7.4734(1.6); 7.4566 (0.7); 7.3410 (0.6); 7.3369 (0.7); 7.3201 (1.2); 7.3030(0.7); 7.2990 (0.7); 7.2823 (0.4); 7.1775 (2.7); 7.1558 (4.9); 7.1343(2.4); 7.1184 (2.1); 7.0968 (3.8); 7.0753 (1.8); 6.7138 (0.9); 6.6923(1.6); 6.6708 (0.8); 6.6206 (0.9); 6.6033 (3.4); 6.5859 (3.4); 6.5686(0.9); 6.0424 (0.4); 6.0253 (1.2); 6.0080 (1.2); 5.9912 (0.3); 5.7579(16.0); 3.7734 (0.5); 3.7573 (0.5); 3.7377 (1.3); 3.7217 (1.3); 3.7039(1.4); 3.6864 (1.4); 3.6679 (0.5); 3.6505 (0.5); 3.3289 (85.5); 2.9222(1.4); 2.9055 (1.5); 2.8830 (2.3); 2.8663 (2.3); 2.7669 (2.2); 2.7521(2.2); 2.7277 (1.4); 2.7128 (1.4); 2.6766 (0.7); 2.6722 (0.9); 2.6677385.2 (0.7); 2.5254 (3.2); 2.5118 (57.1); 2.5077 (111.3); 2.5032(144.5); 2.4988 (106.4); 2.4946 (53.5); 2.3343 (0.6); 2.3300 (0.9);2.3256 (0.6); 2.0759 (6.4); 1.7456 (13.4); 1.7282 (13.3); 1.7017 (5.3);1.6844 (5.2); 1.0644 (0.4); 1.0469 (0.6); 1.0305 (0.4); 0.4921 (0.5);0.4840 (0.6); 0.4795 (0.6); 0.4723 (1.0); 0.4664 (0.8); 0.4592 (1.0);0.4523 (0.7); 0.4477 (0.9); 0.4366 (0.8); 0.4275 (0.6); 0.3518 (0.7);0.3399 (1.3); 0.3277 (1.9); 0.3159 (1.8); 0.3093 (1.7); 0.2975 (0.9);0.2799 (0.6); 0.2732 (0.6); 0.2683 (0.8); 0.2613 (0.9); 0.2493 (0.6);0.2375 (0.4); 0.2248 (0.3); 0.2114 (0.5); 0.1882 (1.4); 0.1749 (4.2);0.1544 (4.6); 0.1413 (1.1); 0.1182 (0.4); 0.0079 (3.8); −0.0001 (93.5);−0.0082 (3.6); −0.1494 (0.5); −0.2935 (0.6); −0.3048 (1.3); −0.3135(1.4); −0.3254 (2.0); −0.3373 (1.4); −0.3406 (1.4); −0.4767 (1.5);−0.4798 (1.5); −0.4918 (1.9); −0.5032 (1.3); −0.5123 (1.2); −0.5243(0.5) I-019

¹H-NMR (600.1 MHz, CD₃CN, 260K): δ = 8.9092 (0.4); 8.9011 (0.5); 8.8719(13.4); 8.8638 (13.1); 8.6337 (3.0); 8.6257 (2.9); 8.2626 (0.3); 8.1801(0.4); 8.1463 (6.7); 8.0919 (11.9); 8.0774 (0.4); 8.0401 (4.4); 8.0268(0.4); 7.8451 (1.9); 7.7364 (1.9); 7.6992 (7.2); 7.5945 (7.2); 7.5198(3.7); 7.5117 (6.9); 7.5037 (3.5); 7.4297 (0.9); 7.4218 (1.6); 7.4140(0.8); 6.3800 (1.3); 6.3685 (3.9); 6.3568 (3.9); 6.3453 (1.2); 6.0315(0.4); 6.0195 (1.0); 6.0082 (1.0); 5.9967 (0.3); 5.4721 (10.5); 3.6955(0.6); 3.6852 (0.6); 3.6719 (0.8); 3.6613 (0.8); 3.5385 (0.8); 3.5270(0.8); 3.5148 (0.6); 3.5033 (0.6); 3.2206 (0.3); 2.9096 (1.0); 2.8983(1.1); 2.8834 (4.3); 2.8713 (6.3); 2.8597 (4.2); 2.8430 (1.0); 2.8334(0.9); 2.6637 (1.4); 2.3187 (0.5); 2.2901 (183.1); 2.0925 (0.4); 2.0800(0.8); 2.0760 (1.4); 2.0719 (2.0); 2.0677 (1.4); 2.0637 (0.8); 2.0422(0.4); 2.0379 (0.4); 2.0324 (0.4); 2.0233 (0.5); 2.0188 (0.5); 2.0151515.0 (0.5); 2.0112 (0.6); 1.9994 (0.9); 1.9768 (7.1); 1.9692 (124.0);1.9651 (233.3); 1.9610 (332.5); 1.9569 (225.5); 1.9528 (111.7); 1.9441(0.9); 1.8540 (0.7); 1.8500 (1.4); 1.8459 (2.0); 1.8418 (1.5); 1.8376(0.9); 1.8217 (16.0); 1.8100 (15.9); 1.7943 (0.6); 1.7823 (0.5); 1.7497(0.4); 1.7303 (4.0); 1.7188 (3.8); 1.4157 (0.4); 1.3409 (0.6); 1.3050(0.6); 1.2828 (1.1); 1.2749 (0.7); 1.2609 (2.5); 1.2441 (0.3); 1.2066(0.4); 1.0616 (0.4); 1.0509 (0.7); 1.0410 (0.8); 1.0294 (0.6); 0.8814(0.5); 0.5765 (0.6); 0.5642 (1.5); 0.5544 (2.0); 0.5435 (1.6); 0.5349(0.8); 0.5199 (0.4); 0.5168 (0.4); 0.5061 (0.4); 0.5034 (0.4); 0.4922(0.6); 0.4785 (1.2); 0.4714 (1.2); 0.4651 (1.2); 0.4587 (0.8); 0.4512(0.5); 0.3405 (0.6); 0.3314 (0.7); 0.3234 (0.8); 0.3023 (0.8); 0.2933(1.1); 0.2870 (2.0); 0.2795 (2.6); 0.2725 (2.4); 0.2651 (2.1); 0.2567(1.9); 0.2513 (2.0); 0.2435 (2.4); 0.2358 (2.4); 0.2293 (2.5); 0.2218(1.7); 0.2154 (1.0); 0.2063 (0.6); 0.0968 (0.7); 0.0052 (6.4); −0.0001(147.2); −0.0057 (4.2); −0.1002 (0.7); −0.1976 (0.8); −0.2057 (1.8);−0.2138 (2.6); −0.2219 (2.7); −0.2294 (2.0); −0.2377 (0.8); −0.3728(0.9); −0.3808 (2.1); 0.3886 (2.8); −0.3966 (2.5); −0.4045 (1.7);−0.4131 (0.6) I-020

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4561 (2.7); 9.4382 (2.8); 8.9983(15.6); 8.9861 (16.0); 8.3243 (0.3); 8.3166 (0.4); 8.2594 (0.3); 8.2375(4.0); 8.2337 (7.8); 8.2299 (4.6); 8.1748 (12.9); 8.1443 (2.5); 8.1395(7.5); 8.1349 (10.0); 8.1305 (7.1); 8.1258 (2.3); 7.6439 (4.2); 7.6318(8.0); 7.6196 (4.1); 6.0444 (0.5); 6.0272 (2.1); 6.0097 (3.3); 5.9921(2.1); 5.9746 (0.4); 3.3690 (0.4); 3.3572 (2.2); 3.3299 (113.6); 3.3137(35.5); 2.6758 (1.1); 2.6714 (1.5); 2.6668 (1.1); 2.6623 (0.5); 2.5248(4.3); 2.5200 (6.8); 2.5113 (91.1); 2.5069 (184.0); 2.5024 (241.4);2.4978 (173.5); 2.4933 (83.2); 2.3381 (0.6); 2.3337 (1.1); 2.3292 (1.5);2.3247 (1.1); 2.0750 407.1 (0.4); 1.6537 (12.8); 1.6363 (12.8); 0.1459(0.9); 0.0080 (7.2); −0.0002 (210.9); −0.0085 (7.4); −0.1496 (0.9) I-021

¹H-NMR (400.6 MHz, CD3CN, 260K): δ = 8.8212 (7.5); 8.6613 (6.0); 8.6448(4.2); 8.3409 (0.4); 8.3294 (0.4); 8.0535 (16.0); 7.4612 (8.2); 7.3588(4.0); 7.3236 (0.5); 7.0365 (5.3); 6.9590 (4.0); 6.8254 (5.3); 6.6102(0.3); 6.5985 (0.6); 6.3509 (4.5); 6.3336 (14.8); 6.3162 (14.8); 6.2989(4.6); 3.3108 (2.1); 3.2991 (2.1); 3.2530 (2.1); 3.2383 (2.2); 3.1303(1.0); 3.1137 (0.4); 3.0939 (0.3); 3.0780 (0.3); 3.0473 (0.8); 2.9905(1.1); 2.9400 (5.8); 2.5163 (2.0); 2.3306 (432.9); 2.1330 (0.6); 2.1268(0.8); 2.1207 (0.6); 2.0019 (0.3); 1.9956 (0.4); 1.9896 (0.4); 1.9837(0.8); 1.9775 (2.2); 1.9720 (50.3); 1.9659 (100.7); 1.9597 (147.8);1.9535 (100.1); 1.9474 (50.2); 1.9407 (1.7); 1.9343 (0.8); 1.9282 (0.3);1.8065 (10.2); 1.7947 (8.1); 1.7883 (8.2); 1.7726 (12.5); 1.7570 (10.4);1.6513 (1.2); 1.6335 (1.2); 1.1851 (0.6); 1.1686 (0.6); 0.7519 389.1(1.8); 0.5810 (2.2); 0.3130 (7.2); 0.2088 (1.6); 0.1826 (2.1); −0.1001(3.8) I-022

¹H-NMR (400.6 MHz, CD3CN, 260K): δ = 8.8323 (3.2); 8.7611 (1.8); 8.0706(2.8); 7.4919 (8.4); 7.4798 (15.9); 7.4677 (8.0); 6.3900 (1.8); 3.7285(0.7); 3.6435 (0.7); 2.9584 (1.6); 2.3767 (1.1); 2.3653 (0.7); 2.3534(4.8); 2.3265 (638.4); 2.3047 (1.5); 2.2933 (1.2); 2.2832 (0.5); 2.1332(0.4); 2.1270 (0.5); 2.1208 (0.4); 1.9930 (0.5); 1.9868 (0.8); 1.9843(0.9); 1.9778 (1.7); 1.9722 (32.7); 1.9660 (65.4); 1.9598 (95.4); 1.9537(65.6); 1.9475 (32.6); 1.9369 (0.4); 1.8249 (15.9); 1.8080 (16.0);1.7887 (2.0); 1.7825 (1.1); 1.7763 (0.7); 1.1389 (0.6); 0.7432 (1.0);0.4967 (1.4); 0.3501 (3.6); −0.0206 (1.1) 459.0 I-023

¹H-NMR (400.6 MHz, CD3CN, 260K): δ = 8.8577 (13.7); 8.8456 (13.9);8.7878 (8.1); 8.7757 (8.2); 8.0817 (11.5); 8.0145 (6.4); 7.4930 (5.7);7.4809 (11.1); 7.4688 (5.6); 6.7228 (14.2); 6.5710 (2.9); 6.5260 (0.9);6.5086 (3.0); 6.4912 (3.0); 6.4737 (0.9); 6.2020 (0.6); 6.1847 (2.0);6.1673 (2.0); 6.1500 (0.6); 3.8049 (1.0); 3.7891 (1.1); 3.7690 (1.6);3.7532 (1.6); 3.6471 (1.7); 3.6292 (1.8); 3.6112 (1.2); 3.5933 (1.2);3.2619 (0.4); 2.9703 (1.3); 2.9525 (1.3); 2.9313 (3.3); 2.9136 (3.3);2.8856 (3.0); 2.8707 (3.1); 2.8467 (1.2); 2.8317 (1.2); 2.5161 (0.5);2.3296 (131.9); 2.2984 (0.8); 1.9722 (12.7); 1.9660 (25.3); 1.9599(37.3); 1.9537 (25.1); 1.9475 (12.7); 1.7837 (15.9); 1.7778 (9.9);1.7662 (16.0); 1.7604 (9.6); 1.1346 (0.6); 1.1172 (0.8); 1.1010 (0.6);0.5590 (0.4); 0.5462 (1.2); 0.5397 (1.0); 0.5226 (2.6); 0.5023 (3.0);423.1 0.4848 (1.9); 0.4618 (0.4); 0.3713 (0.5); 0.3593 (2.8); 0.3545(2.6); 0.3470 (2.6); 0.3424 (2.6); 0.3304 (0.4); 0.3223 (0.5); 0.3093(0.5); 0.2995 (1.3); 0.2898 (1.8); 0.2865 (1.8); 0.2801 (3.4); 0.2702(2.2); 0.2656 (1.7); 0.2604 (3.6); 0.2516 (1.6); 0.2415 (1.1); 0.2315(0.4); 0.2188 (0.4); −0.1090 (0.6); −0.1212 (1.3); −0.1311 (1.3);−0.1441 (1.5); −0.1490 (1.3); −0.1541 (1.1); −0.1630 (0.7) I-024

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 8.7911 (4.3); 8.7811 (4.3); 8.3108(0.5); 8.2558 (16.0); 7.6034 (5.8); 7.5912 (11.1); 7.5791 (5.6); 7.4212(2.2); 6.3944 (1.6); 6.3781 (1.6); 3.3361 (143.3); 3.2048 (0.7); 3.1884(0.8); 3.1674 (2.9); 3.1502 (3.8); 3.1299 (2.3); 3.1078 (0.7); 3.0927(0.6); 2.6784 (0.3); 2.6738 (0.5); 2.6693 (0.3); 2.5441 (0.9); 2.5272(1.2); 2.5138 (28.0); 2.5094 (57.2); 2.5049 (75.5); 2.5003 (54.5);2.4959 (26.5); 2.3362 (0.3); 2.3317 (0.4); 2.3272 (0.3); 2.0744 (15.4);1.7808 (9.3); 1.7636 (9.2); 0.6367 (1.2); 0.6226 (1.7); 0.6093 (1.3);0.5915 (0.6); 0.3038 (1.4); 0.2653 (1.0); 0.2524 (1.4); 0.2419 (1.6);0.2321 (1.7); 0.2207 (1.3); 0.1986 (0.5); 0.1103 (0.9); 0.0977 (1.8);0.0866 (2.7); 0.0739 (2.9); 0.0638 (2.0); 0.0509 (0.8); −0.0002 (1.3);−0.1997 (0.7); −0.2119 (1.8); −0.2226 (2.4); −0.2347 (2.3); −0.2464(1.5); −0.2589 (0.6) 423.1 I-025

¹H-NMR (400.6 MHz, CD₃CN, 260K): δ = 8.7649 (3.5); 8.7528 (3.6); 8.5659(9.9); 8.5538 (10.1); 8.0266 (8.9); 8.0214 (3.7); 7.4084 (1.0); 7.3963(1.8); 7.3842 (1.0); 7.3737 (2.7); 7.3616 (5.1); 7.3495 (2.5); 7.0865(5.7); 7.0851 (5.7); 6.8358 (2.2); 6.8346 (2.1); 6.7657 (0.7); 6.7487(2.5); 6.7317 (2.5); 6.7147 (0.7); 6.3042 (0.9); 6.2868 (0.9); 3.9189(15.6); 3.9174 (16.0); 3.8648 (6.2); 3.8634 (6.2); 3.2377 (1.5); 3.2354(1.5); 3.2199 (2.0); 3.0822 (5.5); 3.0657 (5.3); 2.3392 (0.4); 2.2999(115.2); 2.2712 (1.3); 1.9478 (0.4); 1.9421 (12.7); 1.9359 (25.2);1.9298 (37.0); 1.9236 (25.4); 1.9175 (12.6); 1.9109 (0.4); 1.8616(11.5); 1.8446 (11.5); 1.7584 (0.4); 1.7500 (4.3); 1.7325 (4.3); 0.6425(0.4); 0.5598 (0.6); 0.5559 (0.6); 0.5519 (0.6); 0.5476 (0.5); 0.5432(0.6); 0.5395 (1.1); 421.15 0.5358 (0.7); 0.5316 (0.6); 0.5270 (0.7);0.5231 (0.7); 0.5193 (0.7); 0.5069 (0.4); 0.2445 (0.4); 0.2363 (0.5);0.2307 (1.1); 0.2251 (0.6); 0.2166 (1.0); 0.2104 (1.4); 0.1950 (1.2);0.1865 (1.2); 0.1815 (1.1); 0.1747 (1.9); 0.1712 (1.4); 0.1647 (1.4);0.1606 (1.9); 0.1540 (1.4); 0.1512 (2.1); 0.1441 (0.9); 0.1406 (1.2);0.1309 (1.0); 0.1182 (0.4); 0.1092 (0.5); 0.0897 (0.7); 0.0810 (0.6);0.0769 (1.1); 0.0684 (1.0); 0.0642 (1.0); 0.0577 (0.8); 0.0528 (1.0);0.0459 (0.8); 0.0413 (0.6); 0.0350 (0.4); −0.0549 (0.4); −0.0630 (0.4);−0.0745 (0.5); −0.0781 (0.5); −0.0866 (0.4); −0.0906 (0.4) I-026

¹H-NMR (400.6 MHz, CD₃CN, 260K): δ = 8.8789 (4.8); 8.8668 (5.0); 8.7786(6.5); 8.7665 (6.7); 8.6796 (3.1); 8.6674 (3.2); 8.0872 (6.5); 8.0769(5.1); 7.9984 (1.5); 7.5007 (1.3); 7.4886 (2.5); 7.4765 (1.3); 7.4298(2.0); 7.4177 (3.8); 7.4056 (2.2); 6.7405 (0.6); 6.7230 (1.9); 6.7054(2.0); 6.6878 (0.6); 6.4072 (0.4); 6.3900 (1.4); 6.3727 (1.5); 6.3556(0.5); 6.1994 (0.9); 6.1821 (0.9); 4.0705 (0.4); 3.8950 (0.6); 3.8506(16.0); 3.7210 (12.1); 3.6921 (0.3); 3.3565 (0.9); 3.3427 (0.9); 3.3177(1.1); 3.3037 (1.2); 3.2594 (1.0); 2.9622 (1.1); 2.9450 (2.0); 2.9347(1.2); 2.9233 (1.0); 2.9060 (2.3); 2.8952 (1.6); 2.7463 (1.5); 2.7257(1.6); 2.7071 (1.1); 2.6864 (1.1); 2.3434 (0.4); 2.3346 (0.5); 2.3305(0.6); 2.2937 (256.4); 2.2652 (2.3); 2.0960 (0.4); 1.9467 (0.8); 1.9412(22.8); 1.9350 (45.5); 1.9288 (67.6); 1.9227 (46.0); 1.9165 (23.3);1.9008 (0.5); 1.8252 (8.1); 1.8075 (8.5); 1.7804 (1.1); 1.7698 (1.1);455.2 1.7570 (6.8); 1.7396 (6.3); 1.7107 (0.4); 0.7623 (0.4); 0.7538(0.8); 0.7418 (0.9); 0.7336 (0.9); 0.7217 (0.9); 0.7134 (0.5); 0.7014(0.3); 0.5184 (0.7); 0.3695 (1.1); 0.3588 (1.1); 0.3467 (1.5); 0.3352(1.7); 0.3250 (1.7); 0.3123 (1.5); 0.3027 (1.4); 0.2938 (1.2); 0.2811(1.1); 0.2718 (1.2); 0.2608 (1.0); 0.2417 (2.4); 0.2246 (1.8); −0.0209(0.4); −0.0334 (0.9); −0.0455 (1.3); −0.0578 (1.3); −0.0684 (0.9);−0.0808 (0.4) I-027

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 8.9325 (7.6); 8.9203 (7.8); 8.7866(13.5); 8.7745 (13.7); 8.3088 (1.0); 8.2551 (12.0); 8.2403 (6.9); 8.1311(0.6); 7.6289 (2.1); 7.6168 (4.1); 7.6050 (5.6); 7.5931 (7.0); 7.5809(3.5); 6.4803 (7.9); 6.3727 (0.6); 6.3557 (2.6); 6.3428 (4.2); 6.3259(3.9); 6.3089 (1.1); 6.2854 (4.8); 3.3465 (530.8); 3.2310 (0.9); 3.2146(0.9); 3.1955 (3.7); 3.1794 (7.1); 3.1631 (3.8); 3.1446 (0.9); 3.1277(1.7); 3.1100 (1.0); 3.0887 (1.8); 3.0710 (1.8); 3.0286 (1.7); 3.0131(1.8); 2.9897 (0.9); 2.9745 (0.8); 2.6783 (0.7); 2.6738 (0.9); 2.6694(0.7); 2.5440 (5.8); 2.5269 (2.7); 2.5134 (61.3); 2.5092 (120.4); 2.5048(155.7); 2.5003 (112.3); 2.4960 (54.9); 2.4722 (27.0); 2.4117 (16.0);2.3359 (0.7); 2.3315 (1.0); 2.3272 (0.7); 2.0731 (1.9); 1.8051 (13.8);1.7880 (13.7); 1.7404 (8.3); 1.7230 (8.2); 0.6159 (0.8); 0.6021 (1.3);0.5832 (1.7); 0.5655 (2.0); 0.5531 (1.2); 0.5491 (1.2); 0.5332 354.2(0.6); 0.2847 (0.4); 0.2758 (0.8); 0.2614 (1.4); 0.2540 (2.1); 0.2395(2.5); 0.2313 (3.2); 0.2248 (2.9); 0.2182 (3.8); 0.2102 (3.4); 0.1979(3.9); 0.1878 (2.1); 0.1773 (1.7); 0.1648 (0.6); 0.1562 (0.8); 0.1451(1.1); 0.1326 (1.7); 0.1243 (1.5); 0.1196 (1.5); 0.1095 (1.6); 0.0922(0.7); −0.0002 (2.1); −0.0363 (0.4); −0.0483 (0.9); −0.0612 (1.1);−0.0725 (1.2); −0.0809 (0.9); −0.0918 (0.4); −0.2220 (0.8); −0.2283(1.1); −0.2332 (1.6); −0.2407 (1.9); −0.2517 (2.3); −0.2635 (2.4);−0.2825 (1.2); −0.2953 (0.9); −0.3073 (0.4) I-028

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 8.9310 (8.7); 8.9188 (8.9); 8.7810(15.7); 8.7689 (16.0); 8.3081 (1.1); 8.2492 (13.2); 8.2376 (7.7); 7.6280(2.4); 7.6161 (8.6); 7.6041 (10.2); 7.5920 (4.1); 6.4594 (13.0); 6.3627(0.6); 6.3458 (2.2); 6.3280 (3.0); 6.3098 (4.1); 6.2925 (3.7); 6.2755(1.0); 6.2571 (7.9); 3.3491 (607.4); 3.2346 (0.6); 3.2179 (0.6); 3.1989(4.4); 3.1918 (4.7); 3.1824 (4.7); 3.1752 (4.6); 3.1563 (0.6); 3.1396(0.6); 3.1244 (0.9); 3.1067 (0.9); 3.0856 (1.8); 3.0680 (1.8); 3.0280(1.7); 3.0127 (1.8); 2.9892 (0.9); 2.9740 (0.8); 2.6787 (0.7); 2.6741(1.0); 2.6695 (0.7); 2.5443 (1.1); 2.5274 (2.6); 2.5140 (62.4); 2.5096(126.6); 2.5051 (166.6); 2.5006 (120.0); 2.4961 (57.9); 2.3408 (0.3);2.3365 (0.7); 2.3318 (1.0); 2.3275 (0.7); 2.2127 (0.7); 2.2000 (1.6);2.1915 (1.7); 2.1790 (3.3); 2.1664 (2.0); 2.1579 (2.0); 2.1419 (2.0);2.1293 (1.1); 2.1206 (1.0); 2.1082 (0.5); 2.0730 (4.1); 1.7942 (14.2);1.7771 (14.2); 1.7300 (8.6); 1.7126 (8.6); 1.1497 (1.0); 380.2 1.1454(1.2); 1.1388 (4.5); 1.1318 (5.1); 1.1259 (2.5); 1.1177 (4.8); 1.1107(5.0); 1.1054 (1.8); 1.1006 (2.4); 1.0894 (3.1); 1.0828 (3.5); 1.0728(1.8); 1.0684 (3.0); 1.0618 (3.1); 1.0522 (1.2); 0.9866 (0.4); 0.9691(2.3); 0.9624 (3.2); 0.9569 (4.8); 0.9520 (5.6); 0.9457 (4.5); 0.9399(3.5); 0.9333 (1.8); 0.9233 (0.5); 0.9153 (1.6); 0.9054 (3.5); 0.8991(3.3); 0.8933 (3.4); 0.8869 (3.4); 0.8757 (0.9); 0.6240 (0.4); 0.6109(1.0); 0.5943 (1.9); 0.5867 (1.7); 0.5744 (2.3); 0.5666 (1.4); 0.5618(1.5); 0.5423 (0.6); 0.2823 (0.4); 0.2731 (0.9); 0.2604 (1.6); 0.2520(2.3); 0.2388 (3.4); 0.2304 (3.4); 0.2183 (4.5); 0.2087 (3.4); 0.1987(4.2); 0.1883 (2.2); 0.1783 (1.9); 0.1658 (0.6); 0.1573 (0.8); 0.1485(1.2); 0.1359 (1.7); 0.1281 (1.5); 0.1230 (1.6); 0.1134 (1.6); 0.1103(1.6); 0.1012 (1.0); 0.0961 (0.7); −0.0002 (1.8); −0.0424 (0.4); −0.0549(0.9); −0.0679 (1.1); −0.0787 (1.2); −0.0870 (1.0); −0.0983 (0.4);−0.2068 (0.8); −0.2128 (1.1); −0.2180 (1.6); −0.2252 (1.9); −0.2357(1.8); −0.2382 (1.8); −0.2481 (1.6); −0.2599 (1.2); −0.2702 (1.1);−0.2789 (1.3); −0.2910 (1.2); −0.3030 (0.8); −0.3154 (0.4) I-029

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 8.9234 (2.9); 8.9131 (3.0); 8.7614(7.0); 8.7496 (7.0); 8.3087 (1.2); 8.2835 (7.1); 8.2657 (2.8); 7.6230(7.9); 7.6109 (15.0); 7.5987 (7.5); 7.4080 (6.3); 7.2095 (2.4); 6.3329(1.0); 6.3168 (1.1); 6.1585 (0.9); 6.1420 (2.4); 6.1251 (2.4); 6.1087(0.8); 3.3479 (632.4); 3.1986 (0.4); 3.1549 (4.2); 3.1469 (4.3); 3.1402(4.1); 3.1094 (1.0); 3.1013 (1.0); 3.0858 (1.6); 3.0694 (2.3); 2.6790(0.7); 2.6744 (1.0); 2.6698 (0.7); 2.6654 (0.4); 2.5446 (1.1); 2.5278(2.7); 2.5143 (62.1); 2.5100 (125.8); 2.5054 (165.0); 2.5009 (118.5);2.4964 (57.2); 2.3367 (0.7); 2.3322 (1.0); 2.3276 (0.7); 2.0735 (16.0);1.8397 (8.8); 1.8229 (9.1); 1.7346 (4.0); 1.7185 (3.8); 0.5874 (0.9);0.5050 (1.6); 0.3200 (0.9); 0.2814 (0.7); 0.2559 (1.0); 0.2501 (1.1);0.2375 (1.0); 0.2249 (1.2); 0.1873 (3.1); 0.1683 (3.1); 0.1482 (1.7);0.1294 (1.8); 0.1223 (1.8); 0.0995 (1.7); 0.0079 (0.4); −0.0002 374.1(4.4); −0.0086 (0.8); −0.0229 (0.9); −0.0331 (1.0); −0.2842 (3.5);−0.2966 (3.5); −0.3087 (2.4); −0.3199 (1.1) I-030

¹H-NMR (400.6 MHz, CD3CN, 260K): δ = 9.1725 (2.8); 8.8398 (4.8); 8.8277(5.3); 8.7807 (8.1); 8.6271 (8.7); 8.4540 (0.4); 8.3589 (2.0); 8.3472(2.0); 8.0861 (14.6); 7.9280 (5.6); 7.6362 (5.3); 7.4566 (2.4); 7.4445(4.9); 7.4191 (14.2); 6.6217 (1.0); 6.6098 (1.8); 6.5980 (1.0); 6.4479(3.9); 6.3412 (3.5); 6.2706 (0.8); 3.5090 (0.6); 3.4929 (0.6); 3.4725(0.7); 3.4571 (0.8); 3.3896 (0.6); 3.3723 (0.9); 3.3537 (0.6); 3.2588(4.0); 3.1144 (16.0); 3.0977 (16.0); 3.0772 (9.4); 3.0602 (8.6); 2.9239(0.3); 2.5205 (0.9); 2.3850 (5.1); 2.3596 (7.9); 2.3274 (746.7); 2.1950(0.7); 2.1393 (0.9); 2.1331 (1.6); 2.1269 (2.1); 2.1208 (1.6); 2.1146(0.9); 2.0963 (0.6); 2.0398 (1.2); 2.0037 (1.1); 1.9963 (1.2); 1.9899(1.2); 1.9838 (2.0); 1.9775 (5.5); 1.9721 (112.5); 1.9660 (226.3);1.9598 (332.9); 1.9537 (229.0); 1.9475 (119.1); 1.9347 (5.7); 1.9322(5.5); 1.9261 (3.8); 1.9198 (3.0); 1.8726 (14.1); 1.8008 (4.9); 1.7946390.1 (5.8); 1.7884 (7.0); 1.7823 (6.9); 1.7760 (7.0); 1.7442 (13.3);1.7147 (9.0); 1.6967 (5.9); 1.5770 (0.5); 1.3764 (0.4); 1.2568 (1.3);1.0766 (0.7); 0.8793 (0.5); 0.6099 (4.0); 0.5180 (4.2); 0.4010 (4.2);0.3184 (2.1); 0.3051 (2.4); 0.2508 (5.0); 0.2397 (5.2); 0.2033 (6.4);0.1810 (6.9); 0.0628 (9.9); −0.0034 (1.1); −0.0162 (0.9); −0.0257 (0.7)I-031

¹H-NMR (400.6 MHz, CD3CN, 260K): δ = 9.0236 (0.3); 8.8364 (1.2); 8.5734(0.6); 8.5583 (0.9); 8.5386 (1.1); 8.2277 (0.8); 8.0696 (0.7); 7.8659(0.8); 7.7241 (0.9); 7.6840 (0.9); 7.6794 (0.9); 7.6719 (1.0); 7.4921(1.4); 7.3984 (0.6); 6.4533 (0.5); 6.1818 (0.6); 6.1577 (0.5); 6.0495(0.4); 3.9046 (2.7); 3.8709 (1.5); 3.8555 (1.1); 3.8170 (3.0); 3.6881(0.4); 3.6779 (0.4); 3.6716 (1.0); 3.6614 (1.0); 3.6550 (1.3); 3.6449(1.3); 3.6385 (1.0); 3.6283 (1.0); 3.6220 (0.4); 3.6118 (0.4); 3.3360(0.5); 3.2629 (1.9); 3.1699 (0.7); 3.1590 (0.7); 3.1513 (2.0); 3.1404(2.0); 3.1328 (2.0); 3.1219 (2.0); 3.1143 (0.8); 3.1035 (0.8); 3.0888(0.4); 3.0348 (1.1); 3.0051 (1.8); 2.9712 (0.7); 2.9664 (0.6); 2.9528(0.5); 2.9377 (0.4); 2.8922 (0.3); 2.8628 (0.8); 2.8558 (1.0); 2.7848(0.7); 2.6143 (1.4); 2.4889 (9.3); 2.1326 (0.4); 2.1264 (0.5); 2.1203(0.4); 1.9966 (0.3); 1.9904 (0.4); 1.9879 (0.3); 1.9841 (0.4); 1.9772353.2 (0.8); 1.9716 (19.4); 1.9655 (39.2); 1.9593 (57.6); 1.9531 (39.3);1.9469 (19.9); 1.9398 (1.0); 1.9381 (1.3); 1.9335 (0.4); 1.9321 (0.4);1.8433 (2.8); 1.8123 (2.6); 1.8005 (2.3); 1.7942 (2.0); 1.7880 (1.7);1.7819 (1.2); 1.7751 (1.0); 1.7574 (0.6); 1.3182 (3.1); 1.3078 (11.2);1.2989 (16.0); 1.2911 (11.6); 1.2819 (13.9); 0.7042 (0.5); 0.5441 (0.4);0.5325 (0.4); 0.5131 (0.5); 0.4388 (0.8); 0.1566 (0.8); 0.0556 (1.5);−0.0780 (0.6) I-032

¹H-NMR (400.6 MHz, CD3CN, 260K): δ = 8.8248 (3.0); 8.7843 (0.9); 8.7809(0.8); 8.7730 (0.7); 8.7697 (0.6); 8.6311 (2.4); 8.0438 (2.4); 7.5656(0.4); 7.5544 (0.6); 7.5334 (2.5); 7.4638 (3.5); 7.2242 (3.4); 6.389.3(2.5); 3.8061 (1.4); 3.7795 (8.5); 3.7411 (16.0); 3.2821 (1.6); 3.2627(1.8); 3.2515 (2.9); 3.0341 (2.3); 2.9486 (1.8); 2.9236 (2.0); 2.8814(1.1); 2.8629 (0.7); 2.7955 (0.4); 2.6419 (0.7); 2.6174 (0.6); 2.3583(13.1); 2.1393 (0.7); 2.1331 (0.8); 2.1270 (0.9); 2.1208 (0.8); 2.1147(0.6); 2.0963 (0.5); 2.0161 (0.4); 2.0100 (0.4); 2.0042 (0.4); 1.9977(0.4); 1.9909 (0.4); 1.9838 (0.7); 1.9776 (1.5); 1.9721 (26.6); 1.9660(53.3); 1.9598 (77.5); 1.9537 (52.8); 1.9475 (26.6); 1.9409 (1.1);1.9322 (0.7); 1.9259 (0.4); 1.8009 (8.7); 1.7887 (7.3); 0.7314 (1.0);0.6335 (1.5); 0.3540 (0.8); 0.3324 (2.6); 0.3199 (4.1); 0.3117 (5.0);0.2993 (5.1); 0.2916 (4.9); 0.1660 (1.1); −0.0906 (2.7) 387.1 I-033

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.6384 (0.9); 9.6206 (0.9); 8.9936(5.2); 8.9814 (5.3); 8.4694 (1.2); 8.4651 (2.2); 8.4609 (1.5); 8.3997(3.0); 8.1847 (4.1); 7.6380 (1.4); 7.6259 (2.6); 7.6137 (1.3); 6.0409(0.7); 6.0234 (1.1); 6.0059 (0.7); 5.7568 (1.8); 3.3283 (32.3); 2.5264(0.5); 2.5130 (10.7); 2.5086 (22.1); 2.5041 (29.3); 2.4995 (21.1);2.4951 (10.2); 2.0875 (16.0); 1.6661 (4.3); 1.6487 (4.3); 0.0079 (0.7);−0.0002 (20.7); −0.0085 (0.7) 460.9 I-034

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4401 (1.5); 9.4219 (1.5); 8.9620(7.4); 8.9499 (7.5); 8.2666 (2.0); 8.2629 (3.6); 8.2592 (2.2); 8.1681(1.9); 8.1636 (3.2); 8.1596 (2.2); 8.1356 (2.4); 8.1314 (3.3); 8.1268(1.7); 7.5985 (2.0); 7.5863 (3.8); 7.5742 (1.9); 6.0359 (1.1); 6.0182(1.6); 6.0005 (1.1); 3.3291 (25.0); 3.3183 (16.1); 2.5264 (0.7); 2.5130(11.3); 2.5087 (21.8); 2.5042 (28.0); 2.4997 (20.4); 2.4954 (10.3);2.3373 (16.0); 2.0767 (0.5); 1.6332 (6.0); 1.6158 (5.9); 0.0079 (0.6);−0.0002 (15.0); −0.0084 (0.7) 421.2 I-035

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.5064 (4.0); 9.4890 (4.1); 9.0776(7.0); 9.0757 (6.5); 9.0722 (7.4); 9.0704 (5.7); 8.5901 (4.9); 8.5846(4.7); 8.5686 (5.3); 8.5631 (5.2); 8.2941 (5.7); 8.2905 (9.8); 8.2868(5.8); 8.2550 (15.4); 8.2020 (5.4); 8.1979 (8.3); 8.1937 (5.5); 8.1524(6.2); 8.1483 (8.5); 8.1437 (4.5); 8.0931 (7.5); 8.0716 (7.0); 8.0700(5.8); 6.1431 (0.6); 6.1258 (2.7); 6.1085 (4.3); 6.0911 (2.8); 6.0739(0.6); 3.3271 (96.5); 2.6775 (0.4); 2.6730 (0.6); 2.6685 (0.4); 2.5084(69.8); 2.5039 (87.0); 2.4995 (62.5); 2.3351 (0.4); 2.3307 (0.6); 1.6533(16.0); 1.6359 (15.9); 0.0078 (2.1); −0.0002 (44.8); −0.0083 (2.1) 431.2I-036

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4626 (2.0); 9.4448 (2.1); 9.1061(16.0); 8.2460 (2.9); 8.2424 (5.1); 8.2388 (3.1); 8.1820 (8.6); 8.1644(2.6); 8.1600 (4.6); 8.1561 (3.3); 8.1421 (3.6); 8.1380 (4.6); 8.1334(2.2); 5.9493 (1.4); 5.9318 (2.2); 5.9144 (1.4); 5.8969 (0.3); 3.3462(0.5); 3.3263 (51.3); 3.3155 (23.1); 2.6719 (0.4); 2.5117 (25.0); 2.5076(47.1); 2.5031 (59.4); 2.4986 (43.0); 2.4944 (21.4); 2.3298 (0.4);2.0754 (0.6); 1.6504 (8.6); 1.6330 (8.5); 0.0077 (1.3); −0.0002 (28.7);−0.008.3 (1.3) 425.1 I-037

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4626 (2.0); 9.4448 (2.1); 9.1061(16.0); 8.2460 (2.9); 8.2424 (5.1); 8.2388 (3.1); 8.1820 (8.6); 8.1644(2.6); 8.1600 (4.6); 8.1561 (3.3); 8.1421 (3.6); 8.1380 (4.6); 8.1334(2.2); 5.9493 (1.4); 5.9318 (2.2); 5.9144 (1.4); 5.8969 (0.3); 3.3462(0.5); 3.3263 (51.3); 3.3155 (23.1); 2.6719 (0.4); 2.5117 (25.0); 2.5076(47.1); 2.5031 (59.4); 2.4986 (43.0); 2.4944 (21.4); 2.3298 (0.4);2.0754 (0.6); 1.6504 (8.6); 1.6330 (8.5); 0.0077 (1.3); −0.0002 (28.7);−0.0083 (1.3) 407.1 I-038

¹H-NMR (600.4 MHz, d₆-DMSO): δ = 9.4514 (1.5); 9.4395 (1.5); 9.1214(16.0); 8.2545 (2.1); 8.2519 (3.9); 8.2494 (2.2); 8.1970 (6.4); 8.1650(2.0); 8.1620 (3.3); 8.1592 (2.3); 8.1382 (2.3); 8.1353 (3.4); 8.1322(1.7); 5.9919 (1.1); 5.9803 (1.8); 5.9687 (1.1); 3.3328 (0.3); 3.3131(18.2); 3.3070 (41.3); 2.5226 (0.5); 2.5194 (0.6); 2.5164 (0.7); 2.5075(14.7); 2.5045 (32.0); 2.5015 (44.7); 2.4985 (32.2); 2.4955 (14.9);2.0722 (0.4); 1.6469 (6.6); 1.6352 (6.6); −0.0002 (2.8) 441.1 I-039

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 8.9992 (0.6); 8.6941 (3.8); 8.6832(3.7); 8.3156 (0.4); 8.2841 (8.4); 8.0634 (0.4); 7.9132 (2.6); 7.7788(0.4); 7.7102 (8.4); 7.6827 (0.4); 7.5875 (2.7); 7.5395 (2.0); 6.0446(1.3); 6.0287 (1.3); 5.7557 (16.0); 4.0560 (1.0); 4.0382 (3.1); 4.0204(3.2); 4.0026 (1.4); 3.9655 (0.9); 3.9426 (0.9); 3.9286 (0.9); 3.9172(0.8); 3.9033 (0.9); 3.8902 (0.9); 3.8820 (0.9); 3.4659 (0.4); 3.3245(138.4); 3.2938 (30.4); 2.7340 (0.6); 2.7057 (0.7); 2.6807 (1.0); 2.6762(1.3); 2.6716 (1.7); 2.6669 (1.4); 2.6625 (1.0); 2.6374 (0.8); 2.6273(0.8); 2.6025 (0.7); 2.5251 (2.8); 2.5203 (4.0); 2.5117 (56.9); 2.5072(118.7); 2.5026 (158.0); 2.4980 (112.1); 2.4935 (52.7); 2.3381 (0.4);2.3339 (0.8); 2.3295 (1.1); 2.3248 (0.8); 2.3203 (0.5); 2.0865 (1.1);2.0748 (0.5); 1.9891 (13.7); 1.7129 (9.9); 1.6958 (9.9); 1.3977 (4.3);1.2350 (0.6); 1.1931 (3.8); 1.1753 (7.6); 1.1576 (3.7); 0.1460 (0.7);0.0080 (5.4); −0.0002 (173.2); −0.0085 (5.5); −0.1496 503.0 (0.7) I-040

¹H-NMR (600.1 MHz, CD3CN, 260K): δ = 8.8901 (5.0); 8.8821 (5.1); 8.5993(3.5); 8.5913 (3.5); 8.0994 (4.6); 8.0579 (3.1); 7.9740 (1.4); 7.9713(2.6); 7.9685 (1.5); 7.8145 (1.0); 7.8118 (1.8); 7.8091 (1.1); 7.6273(1.5); 7.5294 (2.5); 7.5263 (2.8); 7.5177 (2.7); 7.5097 (1.4); 7.4986(2.8); 7.4243 (1.4); 7.4009 (1.0); 7.3929 (1.8); 7.3848 (0.9); 6.4504(0.4); 6.4387 (1.4); 6.4271 (1.4); 6.4154 (0.4); 6.0804 (1.0); 6.0689(1.0); 3.8047 (0.5); 3.7932 (0.9); 3.7815 (0.9); 3.7733 (0.8); 3.7616(0.9); 3.7501 (0.5); 3.2254 (0.6); 3.2133 (0.8); 3.1994 (0.9); 3.1873(0.8); 3.0881 (13.8); 3.0725 (9.4); 3.0231 (0.8); 3.0110 (0.9); 2.9972(0.7); 2.9850 (0.6); 2.3046 (16.0); 1.9866 (1.4); 1.9785 (0.8); 1.9742(1.0); 1.9706 (7.3); 435.1 1.9665 (13.1); 1.9624 (19.3); 1.9583 (13.4);1.9542 (6.8); 1.7377 (4.6); 1.7334 (6.4); 1.7262 (4.8); 1.7217 (6.3);1.1524 (2.1); 1.1407 (4.4); 1.1289 (2.0); 0.6555 (2.9); 0.6436 (6.2);0.6317 (2.8) I-041

¹H-NMR (600.1 MHz, CD3CN, 260K): δ = 8.8918 (0.7); 8.8839 (0.7); 8.5935(6.0); 8.5854 (6.1); 8.1000 (0.6); 8.0572 (5.4); 7.9902 (0.4); 7.8337(1.8); 7.8311 (3.1); 7.8285 (2.0); 7.6435 (2.7); 7.6123 (0.5); 7.5754(0.4); 7.5193 (0.4); 7.4893 (2.5); 7.3911 (1.6); 7.3830 (3.1); 7.3750(1.6); 6.3337 (0.4); 6.3299 (0.3); 6.2368 (1.1); 6.2247 (1.6); 6.2131(1.6); 6.2016 (0.5); 6.1448 (0.4); 6.1409 (0.3); 5.4730 (14.2); 4.2271(0.4); 4.2228 (0.4); 4.2177 (0.4); 4.2134 (0.4); 4.2026 (0.7); 4.1931(0.7); 4.1818 (0.4); 4.1782 (0.4); 4.1727 (0.7); 4.1646 (0.4); 4.1593(0.4); 4.1393 (0.5); 4.1342 (0.5); 4.1257 (0.4); 4.1205 (0.4); 3.1132(0.3); 3.0842 (2.1); 3.0718 (16.0); 2.3019 (6.0); 1.9863 (1.3); 1.9782(0.8); 1.9740 (1.0); 1.9703 (7.2); 1.9662 (13.0); 1.9621 (19.1); 1.9580(13.2); 1.9539 (6.8); 1.7637 (0.8); 1.7519 (0.9); 1.7179 (5.5); 1.7063(5.5) 471.2 I-042

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4706 (2.6); 9.4527 (2.6); 8.9964(15.4); 8.9843 (15.7); 8.3158 (4.3); 8.2036 (3.8); 8.1998 (7.6); 8.1961(4.8); 8.1761 (12.8); 8.1566 (3.9); 8.1520 (6.7); 8.1481 (4.3); 8.1073(4.3); 8.1029 (6.4); 8.0986 (3.4); 7.6417 (4.1); 7.6295 (7.9); 7.6174(3.9); 6.0432 (0.4); 6.0264 (2.0); 6.0088 (3.1); 5.9913 (2.0); 5.9737(0.4); 5.7562 (16.0); 3.3247 (140.3); 3.3009 (2.3); 3.0337 (0.6); 3.0217(1.4); 3.0140 (1.5); 3.0092 (0.9); 3.0023 (2.8); 2.9902 (1.5); 2.9826(1.4); 2.9704 (0.7); 2.6756 (1.2); 2.6710 (1.6); 2.6665 (1.2); 2.6621(0.6); 2.5245 (4.9); 2.5195 (7.7); 2.5110 (97.6); 2.5066 (198.7); 2.5021(261.0); 2.4975 433.1 (186.2); 2.4931 (89.1); 2.3379 (0.5); 2.3335(1.1); 2.3289 (1.6); 2.3244 (1.2); 2.3200 (0.5); 1.6559 (13.1); 1.6385(13.0); 1.6113 (0.5); 1.2124 (0.3); 1.1880 (1.7); 1.1800 (3.8); 1.1768(3.8); 1.1716 (3.4); 1.1685 (3.9); 1.1601 (2.4); 1.1400 (0.5); 1.1287(0.7); 1.1157 (0.8); 1.1088 (1.2); 1.0967 (3.5); 1.0892 (3.1); 1.0767(3.4); 1.0718 (2.4); 1.0560 (0.6); 0.0078 (0.4); −0.0003 (11.3); −0.0086(0.4) I-043

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4616 (2.9); 9.4438 (2.9); 8.9854(15.7); 8.9732 (16.0); 8.3163 (0.6); 8.2581 (3.8); 8.2543 (7.6); 8.2505(4.8); 8.2164 (3.8); 8.2119 (6.7); 8.2077 (3.7); 8.1676 (13.0); 8.1582(0.4); 8.1526 (0.6); 8.1450 (4.7); 8.1400 (2.1); 8.1323 (5.2); 8.1275(3.1); 8.1226 (5.4); 8.1173 (5.5); 8.1131 (8.2); 8.1095 (8.1); 7.9671(0.4); 7.9448 (0.4); 7.6250 (4.2); 7.6129 (8.0); 7.6007 (4.0); 7.5303(0.6); 7.5225 (4.8); 7.5173 (1.6); 7.5004 (9.0); 7.4838 (1.9); 7.4784(4.6); 7.4705 (0.4); 7.1652 (0.4); 7.1430 (0.4); 6.0192 (0.4); 6.0018(2.2); 5.9843 (3.4); 5.9669 (2.2); 5.9495 (0.5); 5.7566 (2.0); 4.0558(0.9); 4.0380 (2.9); 4.0202 (2.9); 4.0024 (1.0); 3.8390 (1.5); 3.3256(188.6); 2.6761 (1.3); 487.2 2.6716 (1.8); 2.6670 (1.3); 2.6626 (0.6);2.5250 (4.4); 2.5202 (7.0); 2.5115 (104.1); 2.5071 (215.8); 2.5026(286.4); 2.4981 (203.2); 2.4936 (95.5); 2.3384 (0.6); 2.3338 (1.2);2.3295 (1.7); 2.3249 (1.2); 1.9892 (12.5); 1.6448 (13.1); 1.6274 (13.1);1.1929 (3.5); 1.1751 (6.9); 1.1573 (3.3); 0.1457 (0.7); 0.0078 (5.4);−0.0003 (166.6); −0.0086 (5.3); −0.1496 (0.7) I-044

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4633 (2.1); 9.4453 (2.2); 8.9942(14.3); 8.9820 (14.6); 8.3159 (0.4); 8.1928 (3.0); 8.1890 (6.6); 8.1851(4.4); 8.1763 (11.1); 8.1679 (3.8); 8.1631 (5.3); 8.1592 (3.2); 8.0829(3.6); 8.0785 (5.4); 8.0741 (3.1); 7.6385 (3.8); 7.6263 (7.3); 7.6142(3.7); 6.0432 (0.4); 6.0260 (1.6); 6.0084 (2.6); 5.9909 (1.7); 5.9732(0.4); 5.7563 (12.8); 3.4394 (1.8); 3.4211 (6.4); 3.4027 (6.4); 3.3843(1.9); 3.3252 (156.6); 2.6803 (0.4); 2.6758 (0.9); 2.6712 (1.2); 2.6667(0.9); 2.6622 (0.4); 2.5248 (3.6); 2.5201 (5.1); 2.5114 (70.2); 2.5069(146.5); 2.5023 (194.1); 2.4977 (136.5); 2.4931 (63.6); 2.3382 (0.4);2.3337 (0.8); 2.3291 (1.2); 421.1 2.3245 (0.9); 2.3199 (0.4); 1.6552(10.3); 1.6378 (10.2); 1.1240 (6.9); 1.1056 (16.0); 1.0872 (6.6); 0.1459(0.4); 0.0079 (3.0); −0.0002 (100.0); −0.0086 (3.0); −0.1497 (0.4) I-045

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.0424 (2.9); 9.0243 (3.0); 8.9883(15.7); 8.9762 (16.0); 8.1614 (0.7); 8.1508 (12.8); 7.7165 (0.4); 7.6967(0.4); 7.6357 (4.2); 7.6291 (0.7); 7.6235 (8.0); 7.6114 (4.0); 7.2808(6.1); 7.2771 (10.4); 7.2617 (2.2); 7.2558 (2.4); 7.0973 (1.8); 7.0926(2.6); 7.0880 (1.7); 7.0719 (1.9); 7.0678 (2.4); 5.9898 (0.6); 5.9723(2.5); 5.9546 (3.7); 5.9369 (2.4); 5.9195 (0.5); 3.3265 (74.6); 2.6765(0.5); 2.6719 (0.7); 2.6673 (0.5); 2.5252 (1.7); 2.5205 (2.5); 2.5117(40.3); 2.5074 (84.0); 2.5029 (112.1); 2.4984 (80.3); 2.4940 (38.5);2.3342 (0.5); 2.3296 (0.7); 2.3252 (0.5); 1.9970 (0.6); 1.9847 (1.2);1.9762 (1.4); 1.9639 (2.5); 353.2 1.9515 (1.5); 1.9429 (1.4); 1.9307(0.7); 1.6302 (14.4); 1.6214 (2.1); 1.6128 (14.3); 1.0126 (1.7); 1.0019(4.5); 0.9962 (4.8); 0.9861 (2.5); 0.9810 (4.7); 0.9753 (4.6); 0.9653(2.0); 0.7552 (2.0); 0.7449 (5.0); 0.7396 (5.0); 0.7326 (4.8); 0.7274(5.2); 0.7164 (1.6); 0.0080 (1.8); −0.0002 (57.6); −0.0084 (1.9) I-046

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.1918 (1.2); 9.1740 (1.2); 8.9885(6.0); 8.9763 (6.2); 8.1578 (5.1); 7.6355 (2.7); 7.6321 (3.3); 7.6276(4.1); 7.6230 (5.7); 7.6112 (1.6); 7.5602 (1.7); 7.5559 (2.7); 7.5516(1.5); 5.9771 (0.9); 5.9595 (1.4); 5.9419 (0.9); 3.6743 (0.4); 3.6578(1.0); 3.6411 (1.4); 3.6245 (1.0); 3.6079 (0.4); 3.3281 (34.7); 2.5258(0.7); 2.5210 (1.0); 2.5121 (15.7); 2.5078 (33.0); 2.5033 (44.3); 2.4987(32.1); 2.4943 (15.6); 1.6294 (5.4); 1.6120 (5.3); 1.2679 (0.6); 1.2530(16.0); 1.2365 (15.6); 0.0079 (0.3); −0.0002 (11.0); −0.0085 (0.4) 403.2I-047

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.0296 (0.4); 8.9668 (1.9); 8.7217(0.4); 8.7106 (0.4); 8.3157 (0.8); 8.2511 (16.0); 8.1933 (2.2); 8.1773(2.5); 7.8799 (1.6); 7.8648 (2.9); 7.8453 (2.2); 7.7984 (4.0); 7.7811(2.5); 7.6369 (2.5); 6.3575 (0.8); 5.7559 (4.5); 5.3244 (0.3); 3.3253(246.8); 2.8570 (1.4); 2.7329 (0.3); 2.6762 (1.7); 2.6716 (2.2); 2.6670(1.7); 2.6625 (0.9); 2.5251 (7.4); 2.5203 (10.7); 2.5117 (121.2); 2.5072(243.2); 2.5027 (317.5); 2.4981 (224.0); 2.4936 (104.5); 2.3386 (0.5);2.3340 (1.2); 2.3295 (1.8); 2.3249 (1.2); 2.3204 (0.5); 2.0095 (0.6);1.9905 (0.6); 1.7682 (8.0); 1.7531 (8.1); 1.4278 (0.4); 1.4097 (0.4);1.2.754 (4.4); 0.8709 (0.4); 0.8542 (1.2); 0.8365 (0.5); 0.4997 (0.8);0.2089 (1.8); 0.1458 (1.0); 0.0080 (1.5); −0.0002 (42.1); −0.0085 (1.3);−0.3017 (0.8); −0.4709 (0.8) 481.2 I-048

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.3002 (2.6); 9.282.3 (2.6); 9.0007(15.7); 8.9885 (16.0); 8.6185 (5.5); 8.6121 (5.4); 8.1889 (3.5); 8.1844(5.4); 8.1803 (4.1); 8.1713 (12.4); 8.1602 (0.4); 8.0986 (3.8); 8.0937(6.7); 8.0888 (3.5); 7.8124 (6.0); 7.8083 (5.9); 7.7181 (4.0); 7.7139(6.0); 7.7099 (3.8); 7.6421 (4.3); 7.6299 (8.1); 7.6177 (4.1); 6.6022(4.1); 6.5977 (4.7); 6.5961 (4.8); 6.5915 (4.0); 6.0400 (0.4); 6.0229(2.0); 6.0053 (3.1); 5.9877 (2.0); 5.9703 (0.4); 5.7576 (4.7); 3.3289(35.3); 2.6773 (0.3); 2.6729 (0.4); 2.5264 (1.3); 2.5216 (2.1); 2.5130(26.5); 2.5085 (53.7); 2.5040 (70.2); 2.4994 (50.0); 2.4948 (23.6);2.3308 (0.4); 2.3261 (0.3); 1.6577 395.2 (12.0); 1.6403 (11.9); −0.0002(9.2) I-049

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.3933 (10.8); 9.3435 (2.2); 9.3256(2.2); 9.0014 (12.8); 8.9893 (13.0); 8.2982 (10.8); 8.2102 (2.8); 8.2056(4.8); 8.2018 (3.7); 8.1769 (3.8); 8.1719 (16.0); 8.1675 (3.3); 7.8513(3.3); 7.8472 (5.2); 7.8432 (3.3); 7.6440 (3.5); 7.6318 (6.6); 7.6197(3.3); 6.0431 (0.4); 6.0257 (1.7); 6.0082 (2.6); 5.9907 (1.7); 5.9734(0.4); 5.7569 (3.9); 3.3279 (8.0); 3.0003 (0.3); 2.9866 (0.4); 2.9824(0.4); 2.9743 (0.3); 2.9684 (0.4); 2.9538 (0.6); 2.6770 (0.4); 2.6726(0.5); 2.6681 (0.4); 2.5429 (2.0); 2.5260 (1.4); 2.5212 (2.2); 2.5125(29.0); 2.5081 (58.9); 2.5036 (77.3); 2.4990 (55.5); 2.4945 (26.8);2.3350 (0.4); 2.3304 (0.5); 2.3259 396.1 (0.4); 2.1804 (2.4); 1.6580(10.2); 1.6407 (10.2); 1.4977 (0.3); 1.2338 (0.4); 0.9887 (0.6); 0.9708(1.3); 0.9529 (0.6); −0.0002 (9.7); −0.0085 (0.3) I-050

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.0852 (2.4); 9.0672 (2.4); 8.9890(15.8); 8.9769 (16.0); 8.1530 (12.3); 7.6371 (4.3); 7.6250 (8.1); 7.6128(4.1); 7.5261 (3.6); 7.5216 (5.7); 7.5174 (3.9); 7.3488 (3.1); 7.3450(6.1); 7.3413 (3.6); 7.3113 (3.7); 7.3068 (5.7); 7.3025 (3.0); 5.9878(0.4); 5.9706 (2.0); 5.9530 (3.1); 5.9353 (2.0); 5.9179 (0.4); 3.3263(15.6); 2.5260 (0.7); 2.5213 (1.1); 2.5126 (18.8); 2.5082 (39.1); 2.5036(52.0); 2.4990 (36.6); 2.4944 (17.0); 2.0764 (1.2); 1.9993 (0.6); 1.9865(1.2); 1.9782 (1.3); 1.9743 (0.9); 1.9657 (2.5); 1.9571 (0.8); 1.9531(1.4); 1.9448 (1.3); 1.9321 (0.7); 1.6277 (12.3); 1.6103 (12.2); 1.0088(1.6); 0.9981 (3.9); 369.2 0.9925 (4.1); 0.9880 (2.1); 0.9822 (2.2);0.9771 (4.0); 0.9714 (3.9); 0.9614 (1.8); 0.7568 (1.9); 0.7464 (4.3);0.7410 (4.1); 0.7340 (4.1); 0.7288 (4.3); 0.7177 (1.4); −0.0002 (4.1)I-051

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4752 (2.5); 9.4573 (2.6); 8.9916(15.7); 8.9795 (16.0); 8.1928 (3.5); 8.1886 (6.0); 8.1842 (4.8); 8.1779(12.7); 8.1664 (4.4); 8.1626 (7.4); 8.1588 (3.5); 8.0437 (4.0); 8.0394(6.2); 8.0350 (3.4); 7.6351 (4.2); 7.6229 (8.2); 7.6108 (4.1); 6.0442(0.4); 6.0269 (2.0); 6.0094 (3.1); 5.9918 (2.0); 5.9745 (0.4); 4.0562(0.8); 4.0384 (2.6); 4.0206 (2.6); 4.0028 (0.9); 3.6102 (0.8); 3.5933(2.1); 3.5762 (3.0); 3.5592 (2.2); 3.5422 (0.8); 3.3253 (60.0); 2.6766(0.4); 2.6720 (0.6); 2.6676 (0.4); 2.5256 (1.4); 2.5208 (2.3); 2.5122(35.3); 2.5077 (72.2); 2.5031 (94.8); 2.4985 (66.3); 2.4940 (30.3);2.3345 (0.4); 2.3299 (0.6); 2.3255 435.2 (0.4); 1.9895 (11.5); 1.9098(0.3); 1.6575 (12.1); 1.6401 (12.0); 1.3519 (1.0); 1.2991 (0.8); 1.2591(1.2); 1.2342 (1.8); 1.2162 (0.4); 1.1933 (3.6); 1.1778 (15.9); 1.1757(12.5); 1.1682 (15.8); 1.1608 (15.7); 1.1580 (7.7); 1.1512 (14.8);0.8892 (0.3); 0.8537 (1.0): 0.8370 (0.9): −0.0002 (8.0) I-052

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.5221 (2.5); 9.5041 (2.6); 8.9684(15.6); 8.9563 (16.0); 8.3160 (0.3); 8.2354 (12.5); 7.6427 (4.2); 7.6305(8.0); 7.6184 (4.1); 7.4938 (0.4); 7.4851 (4.1); 7.4796 (1.5); 7.4730(4.4); 7.4679 (2.6); 7.4625 (5.5); 7.4561 (1.8); 7.4505 (5.2); 7.4418(0.6); 7.3616 (9.2); 7.3375 (0.6); 7.3289 (5.4); 7.3233 (1.5); 7.3161(0.8); 7.3116 (1.7); 7.3072 (8.4); 7.3020 (1.7); 7.2906 (1.4); 7.2850(4.0); 7.2763 (0.4); 5.9072 (0.4); 5.8898 (2.1); 5.8721 (3.2); 5.8545(2.1); 5.8371 (0.4); 5.7564 (1.8); 3.3260 (117.6); 2.6898 (0.5); 2.6758(0.7); 2.6713 (0.9); 2.6668 (0.7); 2.5249 (2.2); 2.5201 (3.2); 2.5114(54.5); 2.5069 (112.9); 2.5024 (149.3); 2.4978 (105.4); 2.4933 (49.1);2.3337 (0.7); 2.3292 (0.9); 2.3247 (0.7); 1.5704 (12.7); 1.5531 (12.7);−0.0002 (10.7) 447.2 I-053

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.1950 (3.1); 9.1776 (3.1); 9.0571(5.3); 9.0553 (6.0); 9.0516 (5.9); 9.0498 (5.8); 8.5818 (5.1); 8.5762(4.8); 8.5603 (5.4); 8.5547 (5.4); 8.2380 (16.0); 8.0771 (6.2); 8.0753(6.3); 8.0556 (5.9); 8.0538 (5.9); 7.4910 (7.2); 7.4874 (4.9); 7.4755(4.1); 7.4728 (4.6); 7.470.3 (4.1); 7.2728 (4.5); 6.0904 (0.5); 6.0731(2.4); 6.0557 (3.7); 6.0383 (2.4); 6.0210 (0.5); 4.3321 (0.4); 3.3282(48.4); 2.6777 (0.4); 2.6732 (0.6); 2.6686 (0.4); 2.5267 (1.6); 2.5221(2.3); 2.5133 (32.6); 2.5088 (67.7); 2.5042 (88.9); 2.4996 (62.6);2.4950 (29.3); 2.3357 (0.4); 2.3311 (0.6); 2.3265 (0.4); 2.0685 (0.7);2.0559 (1.5); 2.0476 (1.5); 2.0436 (1.0); 2.0351 (3.0); 2.0264 (1.0);2.0226 (1.6); 2.0141 (1.6); 2.0016 (0.8); 1.6415 (14.3); 1.6240 (14.2);1.4770 (0.5); 1.2727 (0.4); 1.2332 (0.6); 1.0496 (1.9); 1.0385 (5.0);1.0329 (5.3); 1.0289 (2.6); 1.0224 (2.6); 1.0175 (5.1); 1.0119 (5.1);1.0016 443.2 (2.1); 0.7952 (2.2); 0.7846 (5.6); 0.7793 (5.6); 0.7722(5.2); 0.7670 (6.1); 0.7555 (1.8); 0.1458 (0.4); 0.0080 (3.3); −0.0002(112.0); −0.0086 (3.5); −0.1495 (0.4) I-054

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.1340 (3.0); 9.1166 (3.1); 9.0625(5.7); 9.0606 (6.1); 9.0570 (6.2); 9.0551 (5.7); 8.5837 (5.4); 8.5781(5.2); 8.5622 (5.8); 8.5567 (5.7); 8.3162 (0.4); 8.2315 (16.0); 8.0752(6.5); 8.0733 (6.5); 8.0537 (6.2); 8.0518 (6.1); 7.5795 (4.7); 7.5750(7.1); 7.5707 (5.1); 7.4043 (4.2); 7.4005 (7.7); 7.3968 (4.3); 7.3255(4.5); 7.3211 (7.2); 7.3167 (3.9); 6.0759 (0.5); 6.0587 (2.4); 6.0413(3.8); 6.0239 (2.4); 6.0067 (0.5); 5.7564 (0.8); 3.3246 (101.5); 2.6806(0.4); 2.6760 (0.9); 2.6715 (1.3); 2.6669 (0.9); 2.6624 (0.4); 2.5250(3.6); 2.5204 (5.2); 2.5116 (70.6); 2.5071 (145.8); 2.5025 (191.5);2.4979 (133.6); 2.4933 (61.3); 2.3385 (0.4); 2.3339 (0.8); 2.3293 (1.2);2.3247 (0.8); 2.3201 (0.4); 2.0750 (0.4); 2.0129 (0.7); 2.0002 (1.5);1.9919 (1.6); 1.9879 (1.0); 1.9794 (3.1); 1.9709 (1.0); 1.9668 (1.7);1.9584 (1.6); 1.9458 (0.8); 1.6256 (14.8); 1.6081 (14.7); 1.0166 (2.0);393.1 1.0055 (5.2); 0.9999 (5.6); 0.9957 (2.6); 0.9895 (2.8); 0.9845(5.6); 0.9789 (5.3); 0.9686 (2.3); 0.7685 (2.4); 0.7579 (5.8); 0.7526(5.7); 0.7455 (5.4); 0.7403 (6.2); 0.7289 (1.9); 0.1459 (0.9); 0.0162(0.3); 0.0141 (0.3); 0.0080 (7.5); −0.0002 (245.4); −0.0086 (7.3);−0.0127 (0.7); −0.1496 (0.9) I-055

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.5479 (3.2); 9.5304 (3.2); 9.0719(5.5); 9.0702 (6.0); 9.0665 (6.0); 9.0647 (5.8); 8.5905 (5.0); 8.5850(4.8); 8.5691 (5.3); 8.5635 (5.3); 8.2634 (6.2); 8.2532 (16.0); 8.2422(10.5); 8.1831 (13.4); 8.1780 (3.7); 8.1660 (2.9); 8.1612 (8.0); 8.1568(1.2); 8.1004 (6.3); 8.0986 (6.4); 8.0789 (5.9); 8.0771 (6.0); 6.1451(0.5); 6.1278 (2.4); 6.1105 (3.8); 6.0930 (2.4); 6.0758 (0.5); 4.0395(0.4); 4.0217 (0.4); 3.3282 (25.1); 2.6785 (0.4); 2.6739 (0.5); 2.6691(0.4); 2.5274 (1.5); 2.5227 (2.1); 2.5140 (28.3); 2.5095 (58.0); 2.5049(75.4); 2.5003 (53.2); 2.4958 (24.8); 2.3363 (0.3); 2.3319 (0.5); 2.3272(0.3); 1.9906 (1.9); 1.6433 (14.6); 1.6260 (14.5); 1.1942 (0.5); 1.1763(1.1); 1.1586 (0.5); 0.1459 (0.4); 0.0080 (3.4); −0.0002 (101.3);−0.0086 (3.1); −0.0120 (0.5); −0.1495 (0.4) 451.1 I-056

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.5024 (2.4); 9.4844 (2.5); 9.0033(15.6); 8.9911 (16.0); 8.2466 (5.2); 8.2255 (7.5); 8.1723 (12.0); 8.1425(0.7); 8.1322 (9.8); 8.1272 (2.8); 8.1151 (2.5); 8.1104 (6.8); 8.1057(1.0); 7.6464 (4.3); 7.6342 (8.2); 7.6221 (4.2); 6.0547 (0.4); 6.0375(1.9); 6.0199 (3.0); 6.0023 (1.9); 5.9850 (0.4); 3.3343 (24.7); 2.5284(0.9); 2.5237 (1.3); 2.5150 (17.3); 2.5106 (34.6); 2.5060 (44.5); 2.5014(31.1); 2.4968 (14.4); 2.0778 (0.4); 1.6481 (11.7); 1.6308 (11.6);0.0079 (1.8); −0.0002 (56.6); −0.0086 (1.9) 427.2 I-057

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.2537 (0.9); 9.2357 (1.0); 8.9948(6.9); 8.9827 (7.0); 8.1608 (4.8); 7.9251 (1.4); 7.9212 (2.8); 7.9174(1.6); 7.8254 (0.8); 7.8205 (2.6); 7.8156 (3.2); 7.8113 (2.6); 7.8063(0.8); 7.6399 (1.8); 7.6277 (3.5); 7.6156 (1.8); 5.9924 (0.7); 5.9749(1.1); 5.9573 (0.7); 3.9466 (16.0); 3.3251 (7.8); 2.5255 (0.6); 2.5208(1.0); 2.5121 (13.6); 2.5076 (28.1); 2.5030 (36.8); 2.4984 (25.9);2.4938 (12.0); 2.1850 (14.8); 2.0756 (0.4); 1.6444 (4.5); 1.6269 (4.5);0.0079 (1.5); −0.0002 (45.7); −0.0086 (1.4) 400.2 I-058

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.5471 (2.7); 9.5288 (2.7); 9.1163(4.8); 9.1111 (4.6); 8.6022 (3.0); 8.5968 (3.0); 8.5807 (3.3); 8.5753(3.3); 8.3186 (6.5); 8.3152 (4.3); 8.2987 (10.3); 8.2263 (3.6); 8.2221(5.7); 8.2183 (3.8); 8.1604 (3.8); 8.1561 (5.7); 8.1520 (3.3); 8.0997(4.7); 8.0782 (4.3); 7.9532 (0.4); 6.4566 (0.9); 6.4427 (1.5); 6.4378(1.9); 6.4243 (2.1); 6.4052 (0.9); 3.9319 (1.1); 3.9062 (3.0); 3.8856(5.0); 3.8710 (3.2); 3.8591 (1.3); 3.8454 (0.9); 3.3407 (36.3); 3.3279(86.9); 3.2787 (0.7); 2.8918 (2.9); 2.7323 (2.6); 2.6768 (0.5); 2.6723(0.6); 2.5077 (74.5); 2.5034 (93.8); 2.4990 (69.1); 2.3344 (0.4); 2.3302(0.6); 2.3258 (0.4); 2.0755 (16.0); 0.1460 (0.4); 0.0075 (4.0); −0.0002(75.9); −0.0082 (4.0); −0.1496 (0.4) 461.2 I-059

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4985 (2.9); 9.4796 (3.0); 9.0227(15.7); 9.0105 (16.0); 8.9372 (1.8); 8.9250 (1.8); 8.4465 (1.7); 8.2789(4.2); 8.2752 (7.6); 8.2715 (4.5); 8.2192 (12.7); 8.1836 (3.9); 8.1791(6.5); 8.1751 (4.5); 8.1473 (4.9); 8.1430 (6.7); 8.1385 (3.5); 8.1162(0.5); 8.1119 (0.8); 8.1073 (0.5); 8.0183 (0.5); 8.0143 (0.8); 8.0097(0.5); 7.9932 (0.6); 7.9894 (0.9); 7.9856 (0.4); 7.7046 (0.5); 7.6925(1.0); 7.6803 (0.6); 7.6714 (4.3); 7.6592 (8.1); 7.6471 (4.2); 6.3425(1.0); 6.3238 (2.3); 6.3086 (2.6); 6.2899 (1.0); 3.9325 (0.8); 3.9070(4.1); 3.8984 (3.9); 3.8879 (4.6); 3.8836 (4.7); 3.8731 (1.0); 3.8579(0.5); 3.4933 (0.3); 3.3264 (81.9); 3.3197 (75.8); 3.3031 (4.9); 3.2817(0.3); 3.2632 (0.4); 2.6762 (0.7); 2.6717 (0.9); 2.6673 (0.6); 2.5251(3.3); 2.5116 437.1 (56.2); 2.5073 (109.3); 2.5028 (139.6); 2.4982(99.0); 2.4938 (47.2); 2.3340 (0.6); 2.3295 (0.9); 2.3251 (0.6); 0.1459(0.4); 0.0080 (3.7); −0.0002 (88.8); −0.0084 (3.2); −0.1495 (0.4) I-060

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.2497 (0.4); 9.2318 (0.5); 8.9815(2.8); 8.9693 (2.8); 8.1610 (2.3); 7.8900 (0.6); 7.8855 (1.0); 7.8811(0.7); 7.8091 (0.7); 7.8053 (1.3); 7.8016 (0.7); 7.6677 (0.7); 7.6632(1.1); 7.6589 (0.7); 7.6262 (0.8); 7.6141 (1.4); 7.6019 (0.7); 5.9906(0.3); 5.9730 (0.5); 5.9554 (0.3); 5.7560 (2.5); 3.3263 (18.7); 2.5209(0.4); 2.5122 (6.4); 2.5077 (13.5); 2.5031 (18.1); 2.4985 (13.0); 2.4940(6.2); 1.6363 (2.1); 1.6189 (2.1); 1.2425 (16.0); −0.0002 (0.7) 417.1I-061

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.5687 (3.1); 9.5510 (3.2); 9.0057(5.5); 9.0039 (6.1); 9.0002 (6.0); 8.9984 (5.8); 8.5692 (5.2); 8.5636(5.0); 8.5477 (5.5); 8.5421 (5.5); 8.3271 (16.0); 8.3158 (0.6); 8.2359(0.4); 8.0723 (6.3); 8.0705 (6.4); 8.0508 (5.8); 8.0489 (6.0); 7.5235(0.5); 7.5148 (5.2); 7.5092 (1.9); 7.5027 (5.6); 7.4975 (3.2); 7.4922(6.6); 7.4857 (2.3); 7.4801 (6.2); 7.4713 (0.8); 7.4632 (0.3); 7.4116(11.1); 7.3346 (0.7); 7.3260 (6.4); 7.3202 (1.8); 7.3133 (1.0); 7.3088(2.2); 7.3041 (10.0); 7.2990 (2.1); 7.2876 (1.8); 7.2820 (5.1); 7.2732(0.4); 5.9977 (0.5); 5.9804 (2.4); 5.9629 (3.9); 5.9454 (2.5); 5.9282(0.5); 5.7561 (0.8); 3.3250 (175.5); 2.6804 (0.6); 2.6758 (1.2); 2.6712(1.7); 2.6666 (1.2); 2.6622 (0.6); 2.5247 (4.8); 2.5201 (7.0); 2.5114(94.9); 2.5069 (195.2); 2.5023 (256.3); 2.4976 (179.6); 2.4931 (83.0);2.3382 (0.5); 2.3337 (1.1); 2.3291 (1.6); 2.3245 (1.1); 2.3199 (0.5);471.2 1.6057 (0.4); 1.5883 (0.6); 1.5708 (14.8); 1.5534 (14.7); 1.2340(0.4); 0.1459 (0.8); 0.0080 (6.4); −0.0002 (205.6); −0.0086 (6.1);−0.1496 (0.8) I-062

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.0807 (5.5); 9.0789 (6.1); 9.0752(6.0); 9.0734 (5.8); 9.0363 (3.2); 9.0180 (3.3); 8.5873 (5.0); 8.5817(4.8); 8.5658 (5.4); 8.5603 (5.4); 8.3270 (0.4); 8.3159 (0.5); 8.2359(16.0); 8.0796 (6.2); 8.0779 (6.3); 8.0581 (5.8); 8.0563 (5.9); 7.7068(0.4); 7.6980 (3.9); 7.6859 (4.2); 7.6808 (2.7); 7.6756 (4.8); 7.6637(4.6); 7.6549 (0.4); 7.4931 (0.8); 7.4846 (6.4); 7.4789 (2.2); 7.4682(12.4); 7.4629 (10.3); 7.4578 (2.2); 7.4535 (0.8); 7.4464 (1.7); 7.4408(5.2); 7.4322 (0.4); 6.1207 (0.5); 6.1034 (2.5); 6.0857 (3.8); 6.0680(2.5); 6.0506 (0.5); 5.7562 (0.4); 3.3258 (193.5); 2.6805 (0.5); 2.6759(1.1); 2.6714 (1.5); 2.6668 (1.1); 2.6622 (0.5); 2.5249 (4.7); 2.5202(6.9); 2.5115 (89.7); 2.5070 (183.5); 2.5024 (240.6); 2.4978 (168.5);2.4932 (77.9); 2.3382 (0.5); 2.3339 (1.0); 2.3292 (1.5); 2.3246 (1.1);2.3202 (0.5); 1.6059 (14.6); 1.5886 (14.6); 1.5710 (0.5); 1.5535 (0.4);471.2 0.1459 (0.7); 0.0161 (0.3); 0.0139 (0.4); 0.0080 (6.1); −0.0002(187.3); −0.0086 (5.4); −0.1496 (0.7) I-063

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4550 (2.4); 9.4373 (2.4); 9.4122(0.4); 8.4873 (4.0); 8.4806 (4.1); 8.2737 (3.5); 8.2700 (6.6); 8.2662(3.9); 8.1678 (3.6); 8.1627 (16.0); 8.1398 (4.2); 8.1355 (5.7); 8.1310(2.8); 7.9784 (1.3); 7.9716 (1.2); 7.9562 (3.7); 7.9494 (3.8); 7.9332(6.3); 7.9322 (6.3); 7.9111 (2.1); 7.5715 (2.8); 7.3890 (5.8); 7.2065(2.9); 6.0004 (0.4); 5.9833 (1.8); 5.9659 (2.7); 5.9484 (1.8); 5.9309(0.4); 5.7563 (0.4); 3.3255 (40.8); 3.3154 (29.1); 2.6765 (0.4); 2.6719(0.6); 2.6673 (0.4); 2.5254 (2.0); 2.5206 (3.0); 2.5120 (36.6); 2.5075(73.5); 2.5030 (95.4); 2.4984 (67.9); 2.4940 (32.4); 2.3343 (0.4);2.3299 (0.6); 2.3252 (0.4); 1.6449 (10.3); 1.6275 (10.3); 1.2342 (0.5);0.0080 (2.1); −0.0002 (65.2); −0.0085 (2.5) 472.1 I-064

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4745 (2.2); 9.4569 (2.3); 8.8398(4.0); 8.8342 (3.9); 8.4567 (2.1); 8.4509 (2.0); 8.4354 (2.4); 8.4295(2.3); 8.2778 (3.4); 8.2739 (6.5); 8.2701 (3.8); 8.2353 (11.0); 8.1683(3.0); 8.1636 (5.3); 8.1597 (3.9); 8.1417 (4.0); 8.1373 (5.5); 8.1329(2.6); 8.0559 (4.4); 8.0545 (4.5); 8.0346 (4.0); 8.0331 (4.1); 6.1354(0.3); 6.1179 (1.6); 6.1006 (2.6); 6.0831 (1.6); 6.0661 (0.4); 3.3258(66.7); 3.3123 (27.6); 2.6766 (0.5); 2.6719 (0.6); 2.6673 (0.4); 2.5255(1.8); 2.5207 (2.8); 2.5121 (36.6); 2.5076 (74.7); 2.5030 (97.3); 2.4984(68.6); 2.4938 (32.0); 2.3345 (0.4); 2.3299 (0.6); 2.3253 (0.4); 2.0755(16.0); 1.6622 (9.8); 1.6448 (9.8); 0.0080 (2.4); −0.0002 (73.0);−0.0086 (2.3) 506.1 I-065

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.3830 (3.2); 9.3652 (3.3); 9.0877(5.7); 9.0859 (6.2); 9.0823 (6.2); 9.0804 (5.9); 9.0466 (7.8); 9.0410(7.8); 8.9352 (7.8); 8.9301 (7.9); 8.5896 (5.3); 8.5840 (5.0); 8.5681(5.6); 8.5625 (5.6); 8.4437 (4.4); 8.4383 (7.8); 8.4329 (4.1); 8.3164(0.7); 8.2574 (16.0); 8.0989 (6.4); 8.0971 (6.4); 8.0774 (6.0); 8.0756(6.1); 7.9493 (1.1); 7.9419 (10.6); 7.9366 (3.6); 7.9251 (3.5); 7.9198(12.2); 7.9124 (1.2); 7.5512 (6.5); 7.5313 (5.8); 6.1735 (0.5); 6.1562(2.3); 6.1387 (3.7); 6.1212 (2.4); 6.1036 (0.5); 3.3251 (155.8); 3.0357(0.4); 2.9717 (0.5); 2.6807 (0.6); 2.6761 (1.3); 2.6716 (1.8); 2.6669(1.3); 2.6625 (0.6); 2.5251 (5.2); 2.5204 (7.4); 2.5117 (99.5); 2.5072(205.8); 2.5026 (271.4); 2.4980 (190.4); 2.4934 (88.1); 2.3385 (0.5);2.3340 (1.2); 2.3294 (1.6); 2.3248 (1.2); 2.3203 (0.5); 1.6717 (14.2);1.6543 (14.2); 1.3360 (2.0); 1.2985 (1.3); 1.2589 (2.0); 1.2497 (3.1);1.2346 (1.6); 0.8533 (0.4); 0.1459 (0.6); 0.0080 (4.5); −0.0001 (158.1);−0.0085 (4.9); −0.1496 (0.6) 480.2 I-066

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.2250 (3.1); 9.2076 (3.2); 9.0659(5.6); 9.0640 (6.1); 9.0604 (6.2); 9.0584 (5.8); 8.5861 (5.3); 8.5806(5.1); 8.5647 (5.7); 8.5591 (5.7); 8.3163 (0.4); 8.2359 (16.0); 8.0810(6.4); 8.0791 (6.3); 8.0595 (6.0); 8.0576 (6.0); 7.5872 (2.8); 7.5835(9.2); 7.5800 (11.4); 7.5760 (9.2); 7.5724 (3.2); 7.4614 (5.0); 7.4568(8.7); 7.4523 (4.4); 6.0848 (0.5); 6.0675 (2.4); 6.0502 (3.7); 6.0328(2.4); 6.0155 (0.5); 3.3242 (36.4); 2.6763 (0.7); 2.6717 (0.9); 2.6671(0.7); 2.5708 (0.4); 2.5470 (0.8); 2.5298 (50.8); 2.5206 (4.3); 2.5118(52.4); 2.5073 (109.4); 2.5027 (144.4); 2.4981 (101.4); 2.4935 (47.1);2.3341 (0.6); 2.3295 (0.9); 2.3249 (0.6); 2.0994 (0.3); 1.6256 (14.4);1.6082 (14.3); 0.1460 (0.3); 0.0080 (2.6); −0.0002 (91.8); −0.0085(2.8); −0.1495 (0.3) 399.1 I-067

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.6774 (3.2); 9.6602 (3.2); 9.0630(5.3); 9.0614 (6.2); 9.0576 (5.8); 9.0558 (5.9); 8.5870 (4.9); 8.5814(4.7); 8.5655 (5.3); 8.5599 (5.3); 8.5151 (4.5); 8.5106 (7.5); 8.5065(5.5); 8.4460 (6.7); 8.4139 (3.8); 8.4099 (5.9); 8.3161 (0.6); 8.2647(16.0); 8.0911 (6.0); 8.0894 (6.4); 8.0697 (5.7); 8.0679 (6.0); 6.1496(0.5); 6.1326 (2.4); 6.1153 (3.8); 6.0980 (2.4); 6.0808 (0.5); 5.7566(4.7); 3.3258 (147.6); 2.6810 (0.5); 2.6764 (1.0); 2.6719 (1.4); 2.6673(1.0); 2.6629 (0.5); 2.5254 (4.0); 2.5207 (5.7); 2.5120 (81.0); 2.5075(169.6); 2.5029 (225.0); 2.4983 (159.0); 2.4938 (74.2); 2.3389 (0.4);2.3343 (1.0); 2.3297 (1.4); 2.3252 (1.0); 2.3208 (0.5); 1.9894 (0.4);1.9807 (0.9); 1.9533 (1.0); 1.6627 (14.6); 1.6453 (14.6); 1.3975 (9.3);0.1459 (0.5); 0.0080 (3.6); −0.0002 (124.3); −0.0086 (3.8); −0.1497(0.5) 485.0 I-068

¹H-NMR (600.4 MHz, d₆-DMSO): δ = 9.6043 (3.3); 9.5928 (3.4); 8.5576(3.3); 8.5558 (3.5); 8.5495 (3.5); 8.5477 (3.4); 8.4740 (4.6); 8.4712(7.6); 8.4684 (5.3); 8.4142 (7.2); 8.3881 (6.4); 8.1583 (14.1); 8.0897(2.1); 8.0866 (2.1); 8.0762 (3.5); 8.0739 (3.5); 8.0636 (2.5); 8.0605(2.5); 7.8587 (5.6); 7.8451 (5.1); 7.4931 (2.7); 7.4917 (2.8); 7.4836(3.0); 7.4807 (2.9); 7.4793 (2.8); 7.4726 (2.7); 7.4712 (2.6); 6.0821(0.5); 6.0703 (2.5); 6.0587 (3.9); 6.0470 (2.6); 6.0353 (0.6); 3.3063(244.6); 3.2784 (0.8); 2.6156 (1.0); 2.6126 (1.7); 2.6096 (1.0); 2.5217(1.9); 2.5186 (3.0); 2.5155 (3.1); 2.5065 (146.4); 2.5036 (306.6);2.5006 (424.4); 2.4976 (327.3); 460.2 2.4947 (171.4); 2.3876 (2.4);2.3846 (3.1); 2.3817 (2.4); 2.3405 (0.4); 2.3235 (0.4); 2.3186 (0.4);2.0722 (1.4); 1.6560 (15.6); 1.6444 (16.0); 0.0052 (0.4); −0.0001(14.2); −0.0056 (0.7) I-069

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.6468 (1.2); 9.6292 (1.2); 9.1202(16.0); 8.4897 (1.7); 8.4853 (2.8); 8.4811 (2.1); 8.4255 (2.5); 8.4090(1.5); 8.4048 (2.2); 8.2121 (5.9); 6.0091 (0.9); 5.9917 (1.4); 5.9742(0.9); 3.3232 (33.6); 2.6717 (0.4); 2.5252 (1.1); 2.5205 (1.6); 2.5118(23.1); 2.5073 (47.9); 2.5027 (63.7); 2.4981 (45.3); 2.4935 (21.2);2.3295 (0.4); 1.6589 (5.5); 1.6415 (5.5); 0.0080 (0.7); −0.0002 (24.6);−0.0085 (0.7) 495.1 I-070

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.3881 (1.1); 9.3731 (1.1); 9.0698(2.9); 9.0644 (2.8); 8.5862 (2.4); 8.5807 (2.3); 8.5647 (2.6); 8.5592(2.5); 8.2479 (7.6); 8.0853 (3.1); 8.0837 (3.2); 8.0637 (4.0); 8.0623(3.8); 8.0599 (2.8); 8.0560 (1.4); 8.0453 (1.2); 8.0416 (2.4); 8.0379(1.4); 7.9911 (1.6); 7.9862 (2.8); 7.9806 (1.5); 7.9059 (2.6); 7.9014(3.8); 7.8972 (2.3); 6.1042 (1.0); 6.0869 (1.5); 6.0696 (1.0); 5.7563(3.0); 3.3264 (66.8); 2.8170 (16.0); 2.6762 (0.4); 2.6717 (0.6); 2.6670(0.4); 2.5252 (1.7); 2.5205 (2.5); 2.5118 (36.1); 2.507.3 (74.1); 2.5027(96.9); 2.4981 (67.6); 2.4936 (31.2); 2.3341 (0.4); 2.3296 (0.6); 2.3249(0.4); 1.6436 (7.3); 1.6262 (7.3); 0.0080 (1.7); −0.0002 (53.8); −0.0086(1.6) 415.1 I-071

¹H-NMR (400.2 MHz, CD3CN): δ = 9.1810 (0.4); 8.9657 (1.2); 8.9079(11.3); 8.8958 (11.5); 8.8800 (0.6); 8.8679 (0.5); 8.0425 (3.0); 8.0377(6.2); 8.0328 (3.5); 7.9954 (9.7); 7.9799 (3.8); 7.9760 (5.3); 7.9714(3.1); 7.9463 (0.8); 7.9409 (4.6); 7.9382 (5.5); 7.9256 (1.7); 7.9206(7.0); 7.9169 (5.2); 7.7594 (0.3); 7.6904 (1.1); 7.6769 (1.1); 7.6421(0.5); 7.6385 (0.4); 7.6264 (1.2); 7.6233 (0.8); 7.6139 (0.9); 7.6081(3.5); 7.6027 (1.2); 7.5929 (1.7); 7.5896 (2.9); 7.5865 (1.8); 7.5710(0.4); 7.5669 (0.3); 7.5490 (4.8); 7.5333 (3.7); 7.5297 (6.9); 7.5160(1.2); 7.5120 (2.7); 7.4920 (3.6); 7.4799 (7.1); 7.4742 (4.1); 7.4697(6.4); 7.4679 (5.8); 7.3441 (0.4); 7.3328 (0.6); 6.1430 (0.6); 6.1256(2.0); 6.1077 (2.9); 6.0899 (2.0); 6.0722 (0.5); 3.4281 (0.7); 3.4106(0.7); 2.4682 (0.4); 2.4635 (0.6); 2.4589 (0.4); 2.1552 (115.4); 2.1529(114.8); 2.1194 (0.6); 2.1133 (0.9); 2.1071 (1.3); 2.1009 (0.9); 2.0947(0.5); 1.9834 (0.4); 1.9717 (1.3); 1.9641 (3.3); 1.9579 (5.2); 1.9522(72.0); 1.9460 (138.0); 1.9399 (195.7); 1.9337 (133.8); 1.9275 (68.4);1.9145 (1.0); 1.7806 (0.4); 1.7745 (0.8); 1.7684 (1.1); 1.7622 (0.8);1.7559 (0.4); 1.6625 (16.0); 1.6541 (1.5); 1.6452 (16.0); 1.3400 (0.5);1.2850 (0.9); 1.2716 (1.6); 1.2612 (0.9); 1.2428 (0.4); 1.2036 (0.5);1.1401 (0.9); 1.1225 (1.6); 1.1050 (0.8); 0.8817 (0.4); 0.1458 (2.3);0.0374 (0.4); 0.0288 (0.6); 0.0215 (0.5); 0.0162 (0.9); 0.0080 (18.7);−0.0002 448.0 (537.6); −0.0086 (19.5); −0.1496 (2.4) I-072

¹H-NMR (600.4 MHz, d₆-DMSO): δ = 9.6186 (3.6); 9.6070 (3.8); 8.9561(4.8); 8.9549 (4.8); 8.9536 (4.8); 8.4838 (2.9); 8.4799 (3.0); 8.4751(5.0); 8.4722 (8.6); 8.4695 (8.4); 8.4657 (3.5); 8.4109 (7.3); 8.3960(4.5); 8.3933 (6.6); 8.2562 (15.4); 8.0904 (5.1); 8.0760 (4.8); 6.1312(0.6); 6.1197 (2.7); 6.1081 (4.2); 6.0965 (2.7); 6.0849 (0.6); 5.7532(1.9); 4.0366 (0.4); 4.0249 (0.4); 3.3082 (102.8); 2.6172 (0.4); 2.6142(0.7); 2.6111 (0.4); 2.5232 (0.9); 2.5201 (1.2); 2.5170 (0.8); 2.5081(53.2); 2.5052 (115.5); 2.5021 (162.1); 2.4991 (124.1); 2.4962 (63.7);2.3891 (0.8); 2.3861 (1.2); 2.3831 (0.9); 1.9888 (1.6); 1.6750 (15.6);1.6634 (16.0); 1.1877 (0.4); 1.1758 (0.9); 1.1639 (0.5); −0.0001 (5.3)528.2 I-073

¹H-NMR (600.4 MHz, d₆-DMSO): δ = 9.6057 (1.8); 9.5940 (1.9); 8.6221(3.3); 8.6178 (3.5); 8.4785 (2.4); 8.4758 (4.1); 8.4728 (2.8); 8.4192(3.7); 8.3984 (2.1); 8.3956 (3.3); 8.2032 (2.5); 8.1989 (2.5); 8.1889(10.6); 8.1843 (2.8); 7.8875 (3.8); 7.8730 (3.4); 6.0136 (1.4); 6.0020(2.2); 5.9904 (1.4); 3.3077 (55.4); 2.6139 (0.4); 2.5229 (0.4); 2.5198(0.5); 2.5168 (0.3); 2.5079 (27.2); 2.5049 (60.3); 2.5019 (85.5); 2.4988(64.6); 2.4958 (32.0); 2.3889 (0.4); 2.3858 (0.6); 2.3828 (0.5); 2.0733(16.0); 1.6494 (8.2); 1.6377 (8.4); −0.0001 (2.8) 494.1 I-074

¹H-NMR (600.4 MHz, d₆-DMSO): δ = 9.6353 (1.1); 9.6239 (1.1); 9.1673(2.6); 9.1650 (2.7); 8.7548 (2.6); 8.7505 (2.8); 8.6578 (1.9); 8.6554(2.0); 8.6536 (1.9); 8.6512 (1.8); 8.4782 (1.6); 8.4752 (2.6); 8.4725(1.9); 8.4252 (2.3); 8.3968 (1.3); 8.3939 (2.0); 8.3913 (1.1); 8.2707(5.0); 5.9947 (0.9); 5.9831 (1.3); 5.9716 (0.9); 3.3084 (34.8); 2.5231(0.7); 2.5200 (1.1); 2.5169 (1.2); 2.5081 (15.1); 2.5051 (32.7); 2.5020(46.5); 2.4989 (35.3); 2.4959 (17.8); 2.3860 (0.3); 2.0735 (16.0);1.6657 (5.4); 1.6541 (5.5); −0.0001 (2.1) 461.1 I-075

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.6456 (3.2); 9.6282 (3.3); 8.8049(5.6); 8.8031 (5.7); 8.7923 (5.8); 8.7904 (5.9); 8.4853 (4.4); 8.4810(7.7); 8.4768 (5.3); 8.4147 (7.0); 8.4085 (5.9); 8.4033 (6.1); 8.3226(5.7); 8.3196 (8.0); 8.3173 (6.1); 8.2498 (16.0); 7.9649 (5.6); 7.9615(5.5); 7.9523 (5.4); 7.9489 (5.3); 6.0824 (0.5); 6.0652 (2.3); 6.0478(3.7); 6.0304 (2.4); 6.0132 (0.5); 3.3235 (90.3); 2.6810 (0.3); 2.6764(0.7); 2.6718 (1.0); 2.6673 (0.7); 2.6628 (0.3); 2.5253 (2.6); 2.5206(4.0); 2.5119 (57.7); 2.5074 (118.8); 2.5029 (156.9); 2.4983 (111.0);2.4937 (52.0); 2.3343 (0.7); 2.3297 (1.0); 2.3251 (0.7); 1.9893 (1.2);1.6591 (14.3); 1.6417 (14.2); 1.3976 (15.5); 1.1934 (0.3); 1.1755 (0.7);1.1577 (0.3); 0.0080 (1.7); −0.0002 (56.1); −0.0085 (1.6) 485.2 I-076

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.5510 (1.8); 9.5327 (1.8); 8.5224(3.8); 8.5090 (3.9); 8.3969 (3.2); 8.3931 (2.2); 8.3606 (2.7); 8.3567(4.4); 8.3520 (2.7); 8.3330 (2.5); 8.3297 (3.7); 8.3155 (0.4); 8.2688(8.8); 7.8128 (4.0); 7.8089 (4.2); 7.7049 (2.9); 7.7003 (2.6); 7.6914(2.8); 7.6868 (2.6); 5.6247 (1.2); 5.6073 (1.9); 5.5898 (1.2); 4.0559(1.2); 4.0381 (3.6); 4.0203 (3.6); 4.0025 (1.2); 3.3222 (60.4); 2.6757(0.6); 2.6711 (0.9); 2.6665 (0.7); 2.5247 (2.3); 2.5200 (3.5); 2.5113(51.8); 2.5068 (107.1); 2.5022 (141.6); 2.4976 (100.1); 2.4931 (46.6);2.3336 (0.6); 2.3291 (0.9); 2.3244 (0.6); 1.9889 (16.0); 1.6421 (7.8);1.6251 (7.8); 1.3978 (1.6); 1.2360 (0.4); 1.1931 (4.4); 1.1804 (0.3);1.1753 (8.7); 1.1575 (4.2); 0.0080 (1.6); −0.0002 (55.1); −0.0086 (1.6)494.1 I-077

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.7257 (3.3); 9.7091 (3.4); 8.5515(4.7); 8.5472 (7.8); 8.5430 (5.9); 8.5010 (7.1); 8.4274 (3.7); 8.4233(6.2); 8.3161 (0.5); 8.2178 (16.0); 7.7943 (8.5); 7.7856 (14.3); 7.7612(14.7); 7.7525 (8.7); 6.1087 (0.5); 6.0915 (2.5); 6.0743 (3.9); 6.0571(2.6); 6.0397 (0.5); 3.3232 (68.2); 2.6807 (0.4); 2.6762 (0.9); 2.6717(1.3); 2.6671 (0.9); 2.6626 (0.4); 2.5252 (3.0); 2.5205 (4.4); 2.5117(71.3); 2.5073 (149.2); 2.5027 (198.4); 2.4981 (141.2); 2.4936 (66.6);2.3387 (0.4); 2.3341 (0.9); 2.3295 (1.2); 2.3249 (0.9); 2.3205 (0.4);2.0752 (2.4); 1.6520 (15.9); 1.6345 (15.8); 1.2591 (0.3); 1.2341 (0.5);0.0081 (0.5); −0.0001 (16.4); 466.1 −0.0084 (0.5) I-078

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.5493 (3.2); 9.5313 (3.2); 8.6193(0.4); 8.5642 (0.5); 8.5162 (8.3); 8.5099 (9.0); 8.4091 (5.9); 8.4053(4.0); 8.3761 (5.3); 8.3721 (7.8); 8.3675 (4.7); 8.3281 (7.5); 8.3241(5.2); 8.3157 (1.3); 8.3089 (2.4); 8.3060 (2.3); 8.3027 (2.3); 8.2998(1.9); 8.2850 (1.9); 8.2787 (1.6); 8.2371 (16.0); 5.4058 (0.5); 5.3883(2.4); 5.3707 (3.8); 5.3529 (2.4); 5.3355 (0.5); 3.3234 (271.5); 2.6800(0.8); 2.6756 (1.8); 2.6711 (2.5); 2.6664 (1.8); 2.6619 (0.8); 2.5246(6.2); 2.5199 (9.0); 2.5112 (141.5); 2.5067 (293.3); 2.5021 (388.8);2.4975 (273.9); 2.4929 (126.9); 2.3380 (0.8); 2.3335 (1.7); 2.3289(2.4); 2.3243 (1.7); 2.3199 (0.8); 2.0745 (7.4); 1.6426 (14.8); 1.6251(14.8); 1.4350 (0.5); 1.4171 (0.5); 0.0081 (0.7); −0.0001 (26.3);−0.0085 (0.7) 496.1 I-079

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.5519 (3.1); 9.5339 (3.2); 8.5087(8.7); 8.5035 (10.0); 8.4467 (4.3); 8.4415 (3.6); 8.4233 (4.3); 8.4180(4.1); 8.4096 (5.8); 8.3657 (4.7); 8.3616 (7.6); 8.3570 (5.1); 8.3390(4.5); 8.3354 (6.7); 8.3156 (1.4); 8.2516 (16.0); 5.4506 (0.5); 5.4335(2.4); 5.4158 (3.7); 5.3981 (2.4); 5.3805 (0.5); 4.0377 (0.6); 4.0200(0.6); 3.3232 (263.4); 2.6800 (0.9); 2.6755 (1.9); 2.6709 (2.6); 2.6663(1.9); 2.6617 (0.9); 2.5244 (6.6); 2.5197 (9.6); 2.5110 (145.7); 2.5065(303.8); 2.5019 (404.0); 2.4973 (286.2); 2.4927 (133.8); 2.3378 (0.8);2.3334 (1.8); 2.3287 (2.5); 2.3241 (1.8); 2.3195 (0.8); 2.0744 (2.7);1.9888 (2.5); 1.6493 (14.5); 1.6318 (14.6); 1.2340 (0.6); 1.1928 (0.7);1.1750 (1.4); 1.1572 (0.7); 0.0080 (0.7); −0.0002 (26.8); −0.0086 (0.8)512.1 I-080

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.5049 (0.6); 9.4870 (0.6); 8.9869(3.8); 8.9747 (3.9); 8.2534 (0.9); 8.2492 (1.3); 8.2448 (0.9); 8.1757(2.9); 8.1292 (0.9); 8.1254 (1.7); 8.1215 (0.9); 7.9579 (0.9); 7.9535(1.4); 7.9490 (0.8); 7.6312 (1.0); 7.6190 (2.0); 7.6069 (1.0); 6.0260(0.4); 6.0085 (0.7); 5.9909 (0.5); 5.7560 (1.3); 3.3309 (33.8); 2.5255(0.5); 2.5207 (0.8); 2.5120 (13.2); 2.5075 (27.2); 2.5030 (35.6); 2.4984(25.0); 2.4938 (11.6); 1.6564 (2.7); 1.6390 (2.7); 1.2480 (16.0);−0.0002 (9.7) 449.1 I-081

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4744 (3.3); 9.4571 (3.4); 8.3420(3.9); 8.3229 (5.5); 8.3211 (6.0); 8.3155 (0.9); 8.3021 (6.5); 8.2739(4.8); 8.2701 (9.4); 8.2663 (5.4); 8.2449 (16.0); 8.2040 (6.3); 8.2020(7.1); 8.1830 (9.6); 8.1809 (7.7); 8.1784 (8.4); 8.1743 (5.5); 8.1445(6.8); 8.1415 (8.6); 8.1366 (8.2); 8.1321 (4.4); 8.1257 (5.4); 8.1237(5.0); 5.9855 (0.5); 5.9684 (2.5); 5.9511 (4.0); 5.9338 (2.5); 5.9165(0.5); 5.7560 (6.0); 3.3248 (99.6); 3.3118 (42.2); 2.6762 (0.7); 2.6716(1.0); 2.6671 (0.7); 2.5251 (2.5); 2.5204 (3.7); 2.5117 (55.2); 2.5072(114.3); 2.5027 (151.0); 2.4981 (106.4); 2.4935 (49.2); 2.3340 (0.7);2.3295 (0.9); 2.3249 (0.7); 431.1 1.6788 (15.3); 1.6615 (15.2); 0.0080(0.3); −0.0001 (11.0) I-082

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4147 (3.8); 9.3971 (3.8); 9.1006(8.5); 9.0951 (8.7); 9.0886 (6.5); 9.0870 (7.0); 9.0832 (6.6); 9.0816(6.3); 8.9736 (8.5); 8.9686 (8.5); 8.5900 (5.0); 8.5844 (4.8); 8.5685(5.3); 8.5629 (5.2); 8.4941 (4.7); 8.4888 (8.1); 8.4835 (4.4); 8.3161(0.7); 8.2604 (16.0); 8.0997 (6.7); 8.0982 (6.8); 8.0782 (6.2); 8.0767(6.3); 8.0477 (6.8); 8.0274 (9.2); 7.9143 (9.5); 7.8936 (7.0); 6.1784(0.6); 6.1611 (2.6); 6.1436 (4.2); 6.1262 (2.7); 6.1094 (0.5); 3.3238(125.2); 2.6757 (1.4); 2.6713 (1.9); 2.6668 (1.4); 2.5246 (6.6); 2.5112(117.5); 2.5069 (230.6); 2.5024 (298.0); 2.4979 (215.5); 2.4935 (105.1);2.3337 (1.4); 2.3292 (1.8); 2.3248 (1.4); 2.0750 (0.5); 1.6779 (15.8);1.6605 (15.8); 0.0079 (0.6); −0.0002 (16.5); −0.0084 (0.6) 464.2 I-083

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.3856 (4.4); 9.3682 (4.4); 9.0832(7.7); 9.0349 (8.1); 9.0307 (8.0); 8.9183 (8.4); 8.5872 (4.2); 8.5825(4.2); 8.5656 (4.6); 8.5613 (4.4); 8.4226 (7.9); 8.3157 (0.7); 8.2561(12.0); 8.0957 (6.4); 8.0744 (5.9); 7.8510 (10.0); 7.8300 (11.6); 7.6167(11.8); 7.5958 (9.9); 7.5310 (0.6); 7.5138 (0.4); 6.1529 (2.9); 6.1353(4.2); 6.1178 (2.8); 6.1013 (0.8); 3.4202 (0.4); 3.3234 (199.9); 3.2527(0.5); 2.7465 (0.4); 2.6714 (3.5); 2.5022 (490.5); 2.3293 (3.2); 2.0743(0.6); 1.6720 (16.0); 1.6547 (15.9); 1.2319 (0.3); −0.0002 (14.0) 430.2I-084

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.3751 (3.8); 9.3576 (3.8); 9.0843(6.8); 9.0805 (6.5); 9.0789 (6.4); 9.0136 (8.2); 9.0080 (8.3); 8.9025(8.4); 8.8975 (8.4); 8.5878 (4.8); 8.5823 (4.7); 8.5663 (5.2); 8.5608(5.1); 8.4056 (4.7); 8.4003 (8.1); 8.3950 (4.5); 8.3157 (0.8); 8.2558(15.5); 8.0970 (6.5); 8.0956 (6.8); 8.0756 (6.0); 8.0741 (6.3); 7.8704(5.6); 7.8652 (2.7); 7.8570 (6.3); 7.8484 (6.8); 7.8402 (2.8); 7.8349(6.1); 7.4032 (6.2); 7.3981 (2.2); 7.3810 (11.6); 7.3640 (2.0); 7.3588(5.6); 6.1690 (0.7); 6.1519 (2.7); 6.1346 (4.2); 6.1171 (2.7); 6.0995(0.6); 3.3241 (224.5); 2.6754 (1.8); 2.6710 (2.4); 2.6667 (1.8); 2.5409(2.0); 2.5242 (9.1); 2.5108 (146.3); 2.5066 (282.9); 2.5021 (365.7);2.4976 (267.2); 2.4934 (133.2); 2.3334 (1.7); 2.3289 (2.3); 2.3245(1.7); 1.6710 (16.0); 1.6536 (16.0); 0.0077 (0.8); −0.0002 (19.0);−0.0084 (0.8) 414.3 I-085

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.0269 (5.9); 8.9974 (1.0); 8.8686(15.6); 8.8565 (16.0); 8.3156 (0.8); 8.0949 (4.0); 8.0905 (6.7); 8.0861(4.1); 8.0329 (14.8); 7.8502 (4.4); 7.8464 (7.8); 7.8426 (4.4); 7.6894(4.5); 7.6851 (6.5); 7.6808 (4.2); 7.5489 (4.1); 7.5367 (7.8); 7.5245(3.9); 7.3747 (0.4); 5.7560 (0.6); 3.4093 (0.8); 3.3918 (2.2); 3.3744(2.3); 3.3568 (1.1); 3.3535 (0.8); 3.3227 (171.9); 3.2950 (35.1); 2.6752(1.7); 2.6707 (2.4); 2.6662 (1.8); 2.5241 (6.9); 2.5193 (10.7); 2.5107(140.1); 2.5063 (282.2); 2.5018 (368.0); 2.4972 (262.8); 2.4927 (125.2);2.3377 (0.8); 2.3331 (1.6); 2.3286 (2.3); 2.3240 (1.6); 1.7037 (2.4);1.6909 (6.0); 1.6834 419.2 (6.5); 1.6717 (2.7); 1.4140 (1.1); 1.4053(3.9); 1.3937 (10.1); 1.3860 (13.8); 1.3739 (4.8); 1.3365 (0.4); 1.1086(2.2); 1.0911 (4.7); 1.0777 (1.7); 1.0736 (3.0); 1.0582 (0.6); 0.0081(1.9); −0.0001 (59.2); −0.0084 (2.0) I-086

¹H-NMR (400.2 MHz, CD3CN): δ = 8.8793 (0.3); 8.8686 (12.1); 8.8564(12.2); 8.2603 (1.3); 7.9799 (9.6); 7.7932 (0.6); 7.7881 (4.5); 7.7854(5.4); 7.7823 (2.6); 7.7724 (1.7); 7.7674 (7.1); 7.7639 (5.4); 7.6384(0.7); 7.6353 (1.4); 7.6322 (0.9); 7.6218 (1.0); 7.6167 (3.6); 7.6120(1.3); 7.6012 (1.8); 7.5981 (3.1); 7.5949 (1.9); 7.5818 (1.0); 7.5646(1.0); 7.5390 (1.0); 7.5343 (4.8); 7.5304 (2.2); 7.5175 (3.7); 7.5144(6.6); 7.5003 (1.2); 7.4960 (2.6); 7.4942 (2.0); 7.4636 (3.7); 7.4515(7.0); 7.4393 (3.5); 7.4192 (3.2); 7.4150 (5.5); 7.4110 (3.8); 7.3421(3.7); 7.3372 (5.2); 7.3333 (4.1); 7.2748 (4.1); 7.2698 (6.7); 7.2649(3.4); 6.0844 (0.5); 6.0670 (2.0); 6.0492 (2.9); 6.0313 (2.0); 6.0138(0.5); 5.4471 (1.5); 4.0857 (1.0); 4.0679 (3.0); 4.0500 (3.0); 4.0322(1.0); 2.6381 (1.0); 2.1526 (22.8); 2.1078 (0.4); 1.9721 (13.5); 1.9648(1.0); 1.9585 (1.6); 1.9528 (20.1); 1.9467 (38.3); 1.9405 (54.8); 1.9343(37.3); 1.9281 (19.0); 1.8480 (0.6); 1.7689 (0.3); 1.6232 (16.0); 1.6059(15.9); 1.3720 (0.5); 1.2845 (0.5); 1.2760 (1.4); 1.2697 (1.5); 1.2214(3.8); 1.2036 (7.6); 1.1857 (3.7); 0.8808 (0.4); 0.1457 (0.8); 0.0079(6.8); −0.0002 (180.8); −0.0087 (5.7); −0.1497 (0.7) 484.1 I-087

¹H-NMR (400.2 MHz, CD3CN): δ = 14.8224 (0.4); 11.6690 (0.5); 8.8990(10.6); 8.8869 (10.6); 8.5569 (1.2); 8.5416 (0.8); 8.5136 (0.4); 7.9858(8.6); 7.9087 (0.6); 7.8630 (2.6); 7.8585 (4.3); 7.8534 (2.7); 7.8100(0.6); 7.7226 (4.4); 7.6443 (1.2); 7.6195 (1.3); 7.5874 (0.8); 7.5090(0.7); 7.4862 (3.6); 7.4740 (6.1); 7.4617 (3.0); 7.3898 (4.8); 6.1182(0.5); 6.1008 (2.1); 6.0830 (3.0); 6.0650 (2.1); 6.0485 (0.8); 4.4684(0.4); 4.4302 (0.5); 3.6567 (0.4); 3.6409 (0.5); 3.1285 (0.6); 3.1111(0.6); 2.8890 (1.6); 2.7715 (1.4); 2.7280 (16.0); 2.4695 (1.9); 2.4648(2.9); 2.4600 (2.0); 2.3217 (0.5); 2.3103 (0.6); 2.2804 (0.5); 2.2496(0.9); 2.2295 (1.0); 2.1600 (581.7); 2.1199 (3.4); 2.1136 (4.1); 2.1074(4.6); 2.1013 (3.1); 2.0950 (2.1); 2.0771 (5.2); 2.0649 (35.3); 2.0064(0.7); 1.9926 (0.8); 1.9643 (18.8); 1.9525 (231.1); 1.9464 (426.8);1.9402 (590.8); 1.9340 (400.7); 1.9279 (204.2); 1.9064 (1.4); 1.8844(0.7); 1.7972 (0.9); 1.7810 (1.3); 1.7749 (2.4); 1.7686 (3.4); 1.7626(2.3); 1.7562 (1.2); 1.6454 (14.9); 1.6281 (15.0); 1.6151 386.2 (0.6);1.5984 (0.7); 1.5102 (0.5); 1.4969 (0.5); 1.4908 (0.6); 1.4085 (1.7);1.4012 (0.6); 1.3906 (1.7); 1.3508 (1.3); 1.3319 (3.9); 1.3137 (3.9);1.2708 (5.9); 1.1996 (1.0); 1.1662 (0.5); 1.1585 (0.6); 1.1482 (0.5):1.1321 (0.6); 1.1266 (0.5); 1.1101 (0.6); 1.0841 (0.5); 1.0272 (0.5);0.9282 (0.6); 0.8815 (1.5); 0.8567 (1.2); 0.8405 (1.1); 0.8120 (0.5);0.1546 (0.8); 0.1457 (7.9); 0.0530 (0.5); 0.0302 (2.4); 0.0080 (107.4);−0.0002 (1799.6); −0.0086 (72.7); −0.0388 (1.7); −0.0702 (0.7); −0.1025(0.6); −0.1076 (0.8); −0.1498 (8.2); −2.3548 (0.5); −3.0454 (0.4) I-088

¹H-NMR (400.2 MHz, CD3CN): δ = 8.8936 (10.7); 8.8814 (10.8); 8.7707(1.9); 7.9883 (9.0); 7.8620 (3.2); 7.8575 (5.5); 7.8532 (3.4); 7.7568(4.0); 7.7530 (5.6); 7.7490 (3.5); 7.6709 (1.3); 7.6541 (1.4); 7.4810(3.1); 7.4689 (5.9); 7.4568 (3.0); 7.3811 (3.8); 7.3771 (5.8); 7.3732(3.7); 6.1231 (0.6); 6.1057 (2.1); 6.0877 (3.1); 6.0699 (2.1); 6.0523(0.6); 5.4479 (3.4); 4.0859 (1.3); 4.0681 (4.0); 4.0503 (4.0); 4.0324(1.4); 2.1673 (21.4); 2.1222 (0.3); 2.1152 (0.3); 2.1085 (0.3); 1.9726(17.1); 1.9536 (11.3); 1.9475 (20.9); 1.9414 (28.7); 1.9352 (20.4);1.9291 (11.2); 1.6774 (0.8); 1.6659 (1.6); 1.6576 (2.0); 1.6415 (16.0);1.6243 (15.8); 1.2695 (1.2); 1.2216 (4.5); 1.2038 (8.7); 1.1860 (4.4);0.9238 (1.3); 0.9184 (1.5); 0.9123 (4.0); 0.9052 (6.3); 0.9011 (4.4);0.8975 (4.2); 0.8939 (5.2); 0.8861 (2.7); 0.8633 (1.2); 0.8495 (2.7);0.8419 (5.1); 0.8345 (3.4); 0.8298 (3.3); 0.8223 (5.5); 0.8150 (3.1);0.8103 (1.7); 0.8037 (1.3); 0.1459 (0.4); −0.0002 (83.7); −0.0079 (7.0);−0.1496 (0.5) 412.2 I-089

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4896 (3.1); 9.4721 (3.2); 8.9998(4.1); 8.9981 (4.0); 8.9962 (4.1); 8.9939 (4.2); 8.5081 (2.5); 8.5021(2.4); 8.4865 (2.8); 8.4804 (2.7); 8.2800 (4.7); 8.2761 (9.3); 8.2723(5.4); 8.2467 (16.0); 8.1721 (4.1); 8.1673 (7.7); 8.1634 (5.6); 8.1461(5.9); 8.1416 (7.8); 8.1372 (4.0); 8.1075 (4.7); 8.0860 (4.3); 6.1477(0.5); 6.1305 (2.3); 6.1131 (3.6); 6.0956 (2.3); 6.0782 (0.5); 4.0565(0.5); 4.0387 (1.6); 4.0209 (1.7); 4.0031 (0.6); 3.3462 (0.4); 3.3264(57.0); 3.3162 (40.1); 2.6772 (0.5); 2.6726 (0.7); 2.6681 (0.5); 2.5261(1.9); 2.5215 (2.7); 2.5127 (38.2); 2.5082 (79.2); 2.5037 (104.2);2.4990 (72.8); 2.4944 (33.7); 2.3350 (0.4); 2.3305 (0.6); 2.3259 (0.4);1.9898 (7.4); 1.6661 (13.9); 1.6487 (13.8); 1.3972 (0.7); 1.2352 (0.4);1.1936 (2.0); 1.1758 (4.1); 1.1580 (2.0); 0.0080 (1.6); −0.0002 (52.5);−0.0086 (1.5) 474.2 I-090

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.5110 (3.8); 9.4938 (3.8); 8.6856(7.4); 8.6794 (7.4); 8.3161 (0.6); 8.2686 (5.1); 8.2621 (4.9); 8.2468(6.0); 8.2398 (8.5); 8.2350 (10.4); 8.2312 (6.1); 8.1564 (4.8); 8.1518(9.1); 8.1476 (5.8); 8.1250 (6.4); 8.1209 (8.5); 8.1165 (4.6); 7.9432(8.0); 7.9214 (7.0); 5.9748 (0.6); 5.9575 (2.9); 5.9402 (4.6); 5.9229(2.9); 5.9054 (0.6); 3.3263 (90.8); 3.3177 (45.7); 2.6814 (0.3); 2.6772(0.7); 2.6726 (0.9); 2.6679 (0.7); 2.6635 (0.3); 2.5260 (3.0); 2.5212(4.6); 2.5126 (55.6); 2.5081 (112.0); 2.5036 (145.2); 2.4990 (102.5);2.4945 (48.3); 2.3348 (0.6); 2.3303 (0.9); 2.3258 (0.6); 2.0758 (5.0);1.6816 (16.0); 1.6641 (15.9); 0.0080 (2.3); −0.0002 (67.4); −0.0085(2.1) 508.2 I-091

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.5384 (2.5); 9.5211 (2.5); 9.0504(15.7); 9.0382 (10.0); 8.2236 (3.7); 8.2198 (6.9); 8.2160 (4.1); 8.1494(3.1); 8.1447 (6.5); 8.1405 (4.6); 8.1315 (5.0); 8.1276 (5.6); 8.1229(2.7); 7.9534 (0.5); 7.7417 (4.2); 7.7296 (7.9); 7.7174 (4.0); 6.0691(0.4); 6.0519 (2.0); 6.0346 (3.1); 6.0172 (2.0); 6.0000 (0.4); 3.3250(61.7); 3.3136 (31.1); 2.8918 (4.0); 2.7329 (3.2); 2.7317 (3.2); 2.6765(0.6); 2.6719 (0.8); 2.6674 (0.6); 2.5255 (2.8); 2.5207 (4.7); 2.5121(52.3); 2.5076 (103.6); 2.5030 (132.7); 2.4984 (92.5); 2.4939 (42.8);2.3344 (0.6); 2.3298 (0.8); 2.3252 (0.6); 2.0868 (0.5); 1.7044 (10.7);1.6870 (10.6); 1.3976 (3.1); 1.1198 (0.3); 0.0080 (2.6): −0.0002 (69.9):−0.0085 (2.1) 475.2 I-092

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.3542 (2.8); 9.3362 (2.8); 8.9979(15.7); 8.9858 (16.0); 8.3159 (0.5); 8.1720 (7.2); 8.1703 (8.5); 8.1254(1.8); 8.1217 (3.4); 8.1180 (2.0); 8.1003 (2.3); 8.0967 (4.4); 8.0929(2.6); 8.0138 (3.2); 8.0095 (6.2); 8.0056 (4.3); 7.9904 (5.2); 7.9863(6.7); 7.9818 (3.4); 7.6429 (3.8); 7.6307 (7.3); 7.6185 (3.7); 6.0446(0.4); 6.0271 (1.5); 6.0095 (2.3); 5.9919 (1.5); 5.9761 (0.3); 5.7560(10.1); 4.3046 (0.6); 4.2935 (0.7); 4.2836 (0.5); 4.2777 (0.8); 4.2682(1.5); 4.2568 (1.2); 4.2415 (1.8); 4.2300 (1.2); 4.2219 (1.3); 4.2158(1.7); 4.2033 (0.6); 4.1955 (1.3); 4.1898 (1.6); 4.1799 (0.7); 4.1691(0.5); 4.1632 (0.6); 4.1595 459.1 (0.6); 4.1537 (0.7); 3.3235 (114.1);2.6799 (0.5); 2.6755 (1.1); 2.6710 (1.5); 2.6665 (1.1); 2.6620 (0.5);2.5245 (4.7); 2.5198 (7.2); 2.5111 (89.7); 2.5066 (182.0); 2.5021(236.9); 2.4975 (168.0); 2.4930 (79.6); 2.3380 (0.5); 2.3334 (1.0);2.3289 (1.4); 2.3243 (1.0); 2.3200 (0.5); 1.7537 (0.4); 1.6526 (12.3);1.6352 (12.3); 0.1459 (0.8); 0.0079 (6.9); −0.0001 (202.2); −0.0085(6.7); −0.0177 (0.3); −0.1496 (0.8) I-093

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4914 (2.6); 9.4736 (2.7); 8.9966(15.7); 8.9844 (16.0); 8.2729 (3.3); 8.2691 (6.9); 8.2653 (4.7); 8.2523(4.2); 8.2477 (6.2); 8.2438 (3.6); 8.1783 (12.4); 8.1650 (4.0); 8.1605(6.4); 8.1561 (3.4); 7.6394 (4.3); 7.6273 (8.1); 7.6151 (4.1); 6.0510(0.4); 6.0335 (2.0); 6.0160 (3.1); 5.9985 (2.0); 5.9809 (0.4); 5.7566(6.8); 5.1388 (1.6); 5.1143 (4.9); 5.0896 (5.2); 5.0649 (1.8); 3.3244(36.1); 2.6763 (0.6); 2.6717 (0.8); 2.6671 (0.6); 2.5251 (2.9); 2.5204(4.7); 2.5117 (49.4); 2.5073 (99.4); 2.5027 (129.4); 2.4981 (92.0);2.4936 (43.5); 2.3563 (1.0); 2.3341 (0.6); 2.3295 (0.8); 2.3250 (0.6);1.7547 (0.8); 1.6591 (12.0); 1.6417 (11.9); 1.2400 (0.4); 0.1457 (0.4);0.0078 (3.4); −0.0003 (91.7); −0.0086 (3.0); −0.1497 (0.3) 475.1 I-094

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.3506 (2.5); 9.3326 (2.5); 8.9994(15.6); 8.9872 (16.0); 8.8459 (3.0); 8.8437 (3.4); 8.8395 (3.4); 8.8373(3.1); 8.3158 (0.8); 8.1928 (2.8); 8.1878 (5.2); 8.1841 (4.4); 8.1715(15.7); 8.1662 (6.6); 8.1613 (2.9); 7.8499 (3.9); 7.8458 (5.9); 7.8418(3.8); 7.6402 (4.2); 7.6280 (8.1); 7.6159 (4.1); 7.4098 (0.6); 7.4017(0.4); 7.3961 (0.4); 7.3870 (0.6); 7.1097 (4.4); 7.1033 (4.4); 6.9934(2.1); 6.0421 (0.4); 6.0248 (1.8); 6.0072 (2.9); 5.9897 (1.9); 5.9722(0.4); 5.7559 (2.9); 3.3218 (77.2); 2.6800 (0.6); 2.6755 (1.4); 2.6709(1.9); 2.6663 (1.4); 2.6619 (0.6); 2.5412 (0.7); 2.5244 (4.8); 2.5197(7.1); 2.5110 (106.0); 2.5065 (219.5); 2.5020 (291.6); 2.4974 (207.3);2.4928 (97.4); 2.4521 (0.6); 2.4355 (0.4); 2.3378 (0.6); 2.3334 (1.3);2.3288 (1.8); 2.3242 (1.3); 2.3197 (0.6); 1.6603 (11.2); 1.6429 (11.2);1.2568 (3.8); 1.2395 (3.8); 1.1613 (2.4); 1.1443 (2.3); 1.1069 (8.0);1.0785 (8.1); 0.9143 (2.4); 0.8976 (2.3); 0.1458 (0.4); 0.0079 (2.7);−0.0002 (89.6); −0.0086 (2.7); −0.1495 (0.3) 461.2^(#) I-095

¹H-NMR (600.1 MHz, CD3CN): δ = 9.2056 (5.4); 8.1732 (3.2); 8.0710 (2.9);8.0509 (4.0); 8.0484 (3.8); 7.8814 (0.7); 7.8702 (0.7); 6.2048 (0.8);6.1932 (1.2); 6.1815 (0.8); 3.2758 (1.6); 3.1333 (0.8); 3.1168 (1.0);3.1009 (16.0); 2.1346 (2.2); 2.1281 (2.4); 2.0727 (0.8); 2.0543 (0.3);2.0503 (0.5); 2.0463 (0.3); 1.9638 (1.8); 1.9556 (1.7); 1.9477 (17.5);1.9436 (31.9); 1.9395 (46.0); 1.9354 (32.3); 1.9313 (16.8); 1.6943(6.4); 1.6828 (6.4); 1.2703 (0.5); 1.2328 (0.4); 1.2219 (0.4); 1.1391(0.4); 0.0052 (1.9); −0.0001 (41.5); −0.0053 (2.2) 474.9 I-096

¹H-NMR (600.1 MHz, d₆-DMSO): δ = 9.43 (d, 1H), 8.81 (d, 2H), 8.21 (m,.1H), 8.14 (m, 1H), 8.13 (m, 2H), 5.94 (m, 1H), 3.31 (s, 3H), 2.32 ( s,3H), 1.63 (d, 3H) 421.0 I-097

¹H-NMR (600.1 MHz, d₆-DMSO): δ = 9.65 (d, 1H), 9.41 (m, 2H), 8.49 (m,1H), 8.42 (s, 1H), 8.41 (s, 1H), 8.27 (s, 1H), 6.09 (m, 1H), 1.67 (d,3H) 528.9 I-098

¹H-NMR (600.1 MHz, d₆-DMSO): δ = 9.4562 (4.1); 8.9168 (0.9); 8.9049(0.9); 8.2334 (3.2); 8.0092 (2.0); 8.0064 (2.1); 7.4498 (2.1); 7.4470(2.2); 6.0021 (0.6); 5.9904 (1.0); 5.9787 (0.6); 3.3324 (16.0); 2.5230(0.5); 2.5200 (0.7); 2.5169 (0.7); 2.5050 (23.5); 2.5020 (32.1); 2.4991(24.6); 2.0744 (2.8); 1.6188 (3.8); 1.6071 (3.8) 402.9 I-099

¹H-NMR (600.1 MHz, CD3CN): δ = 8.7011 (6.6); 8.2650 (1.5); 8.2625 (4.2);8.2594 (6.0); 8.1932 (1.7); 8.1905 (2.7); 8.0383 (0.8); 8.0264 (0.8);7.9730 (6.1); 6.1091 (0.3); 6.0974 (1.3); 6.0856 (2.0); 6.0737 (1.4);6.0620 (0.4); 4.6786 (0.3); 4.0664 (0.4); 4.0545 (0.4); 2.3485 (16.0);2.2392 (0.5); 2.2385 (0.5); 2.2059 (2.2); 2.1777 (0.8); 1.9735 (2.1);1.9674 (13.1); 1.9593 (0.4); 1.9551 (0.4); 1.9513 (2.9); 1.9472 (5.4);1.9431 (7.7); 1.9390 (5.3); 1.9349 (2.6); 1.6725 (9.8); 1.6610 (9.8);1.3730 (0.6); 1.2764 (0.9); 1.2685 (0.5); 1.2164 (0.6); 1.2046 (1.1);1.1927 (0.5) 475.0 I-100

¹H-NMR (600.1 MHz, d₆-DMSO): δ = 9.0012 (12.6); 8.9974 (2.1); 8.9890(12.9); 8.9852 (2.0); 8.7704 (1.8); 8.7516 (1.9); 8.3136 (0.8); 8.1575(9.9); 8.1134 (0.9); 7.6525 (0.4); 7.6467 (2.5); 7.6404 (0.8); 7.6246(6.6); 7.6284 (0.5); 7.6224 (2.4); 7.2785 (0.6); 7.2129 (6.2); 6.0251(0.4); 6.0074 (1.6); 5.9894 (2.2); 5.9714 (1.6); 5.9540 (0.4); 4.4016(0.4); 4.0650 (0.4); 4.0519 (1.6); 4.0140 (16.0); 4.0128 (16.0); 2.8869(0.7); 2.8790 (0.7); 2.7244 (0.4); 2.7128 (0.4); 2.7021 (0.4); 2.2267(146.0); 2.6811 (0.4); 2.6764 (0.8); 2.6718 (1.1); 2.6674 (0.8); 2.6627(0.4); 2.5422 (2.8); 2.5254 (3.4); 2.5207 (5.1); 2.5120 (67.0); 2.5075(127.1); 2.5029 (181.2); 2.4982 (122.9); 2.4928 (65.2); 2.2288 (0.4);2.2242 (0.8); 367.1 2.2297 (1.1); 2.2252 (0.8); 2.0740 (0.5); 1.5915(10.4); 1.5742 (10.4); 1.4824 (1.0); 1.4651 (1.0); 0.0080 (0.4); −0.0002(14.6); −0.0085 (0.5) I-101

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 17.0545 (0.3); 9.6374 (2.5); 9.6192(2.6); 9.0034 (13.0); 8.9913 (13.5); 8.9777 (0.4); 8.7807 (0.3); 8.6946(0.6); 8.6707 (0.7); 8.6592 (0.8); 8.6290 (1.2); 8.5946 (12.8); 8.5905(13.4); 8.5135 (4.0); 8.5095 (6.5); 8.5054 (3.1); 8.4092 (0.5); 8.4052(0.8); 8.3125 (12.6); 8.3029 (0.8); 8.2986 (0.7); 8.2835 (1.0); 8.2790(0.9); 8.1863 (11.2); 7.9766 (0.4); 7.9572 (0.6); 7.8685 (0.4); 7.8577(0.4); 7.6451 (3.7); 7.6330 (6.9); 7.6209 (3.4); 7.1990 (0.4); 7.0711(0.3); 6.9445 (0.4); 6.7796 (0.5); 6.0950 (0.4); 6.0788 (1.9); 6.0609(2.7); 6.0433 (1.8); 3.8041 (0.4); 3.7490 (0.4); 3.7027 (0.4); 3.6812(0.4); 3.6508 (0.4); 3.6138 (0.4); 3.5784 (0.4); 3.5317 (0.6); 3.5121(0.5); 3.4710 (0.6); 451.0 3.4299 (1.2); 3.4204 (1.9); 3.4063 (1.4);3.3875 (6.3); 3.3603 (56.3); 3.3407 (17.0); 3.3241 (1850.4); 3.2543(0.4); 3.2405 (0.4); 3.1852 (0.4); 3.0433 (0.5); 3.0239 (0.9); 2.9943(0.4); 2.9592 (0.4); 2.9002 (0.3); 2.8362 (0.4); 2.7669 (0.5); 2.7470(0.5); 2.7349 (0.5); 2.7119 (1.0); 2.6757 (11.9); 2.6712 (16.0); 2.6667(11.4); 2.6620 (5.4); 2.5415 (155.6); 2.5247 (51.1); 2.5199 (78.5);2.5111 (1031.6); 2.5068 (1994.3); 2.5023 (2533.7); 2.4977 (1815.4);2.4933 (865.9); 2.3977 (0.6); 2.3678 (0.7); 2.3336 (11.6); I-102

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.0196 (15.8); 9.0074 (16.0); 8.7843(0.7); 8.7722 (1.4); 8.7672 (2.3); 8.7565 (0.7); 8.7482 (2.2); 8.7085(3.0); 8.7061 (3.1); 8.6909 (3.1); 8.6884 (3.1); 8.3130 (2.1); 8.1805(11.2); 7.7649 (1.8); 7.7620 (3.1); 7.7593 (1.9); 7.7424 (2.0); 7.7397(3.4); 7.7368 (2.0); 7.6515 (4.2); 7.6393 (8.0); 7.6271 (4.1); 7.5605(0.3); 7.3028 (1.8); 7.3003 (2.0); 7.2859 (2.1); 7.2834 (2.2); 7.2806(1.9); 7.2780 (1.8); 7.2636 (2.0); 7.2611 (2.0); 7.0491 (2.0); 7.0456(2.1); 7.0318 (3.2); 7.0284 (3.2); 7.0146 (1.8); 7.0111 (1.7); 6.9429(7.4); 6.9409 (7.6); 6.0950 (0.4); 6.0777 (1.8); 6.0596 (2.4); 6.0415(1.8); 6.0239 (0.4); 3.3246 (263.2); 2.6808 (0.8); 2.6762 (1.7); 2.6716(2.4); 2.6671 (1.7); 335.1 2.6625 (0.8); 2.5659 (0.3); 2.5420 (13.4);2.5252 (7.4); 2.5205 (11.0); 2.5118 (139.5); 2.5073 (283.8); 2.5027(373.3); 2.4981 (270.1); 2.4935 (130.4); 2.3387 (0.7); 2.3341 (1.6);2.3295 (2.3); 2.3250 (1.6); 2.3205 (0.8); 2.0738 (4.0); 1.6236 (11.8);1.6064 (11.8); 0.0081 (0.6); −0.0001 (21.4); −0.0085 (0.6) I-103

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.0147 (15.7); 9.0026 (16.0); 8.9901(2.1); 8.9780 (2.1); 8.8219 (2.9); 8.8024 (2.9); 8.3130 (3.9); 8.2739(0.4); 8.2542 (0.4); 8.2030 (13.2); 8.1592 (0.5); 8.1224 (3.6); 8.1041(3.9); 8.1008 (4.0); 7.7423 (0.5); 7.7254 (0.6); 7.6937 (1.2); 7.6785(4.3); 7.6610 (3.9); 7.6568 (5.4); 7.6445 (8.2); 7.6324 (4.3); 7.6175(0.6); 7.4873 (0.4); 7.4650 (0.5); 7.4440 (3.0); 7.4261 (3.6); 7.4037(2.4); 7.3807 (1.9); 7.2858 (1.5); 7.2348 (14.3); 6.1097 (0.5); 6.0920(2.2); 6.0736 (3.0); 6.0557 (2.2); 6.0383 (0.5); 5.8445 (0.4); 4.4988(0.6); 4.4875 (0.8); 4.4760 (0.6); 3.9088 (1.2); 3.8999 (1.3); 3.7717(0.6); 3.7603 (0.7); 3.7479 (0.5); 3.4846 (0.5); 3.3251 (471.9); 2.7112(0.4); 2.6803 (1.9); 403.1 2.6760 (4.0); 2.6715 (5.6); 2.6670 (4.1);2.6626 (2.0); 2.6033 (0.4); 2.5420 (92.4); 2.5250 (16.9); 2.5203 (26.7);2.5115 (341.6); 2.5072 (684.5); 2.5026 (896.2); 2.4980 (661.8); 2.4936(328.8); 2.3686 (0.4); 2.3385 (1.8); 2.3340 (3.9); 2.3294 (5.5); 2.3249(4.1); 2.3204 (2.0); 2.0737 (11.3); 1.6436 (14.0); 1.6263 (14.0); 1.4776(2.0); 1.4603 (1.9); 0.0079 (1.2); −0.0002 (39.5); −0.0085 (1.2) I-104

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.3494 (2.5); 9.3308 (2.5); 9.0119(15.8); 8.9998 (16.0); 8.9926 (1.1); 8.9804 (0.8); 8.3126 (5.0); 8.2242(2.1); 8.2191 (2.4); 8.2039 (14.4); 8.0967 (0.3); 8.0660 (0.7); 7.6884(2.2); 7.6838 (2.3); 7.6748 (2.3); 7.6701 (2.2); 7.6639 (4.5); 7.6517(8.1); 7.6395 (4.2); 6.0477 (0.5); 6.0304 (2.0); 6.0127 (3.1); 5.9950(2.1); 5.9781 (0.5); 3.9072 (0.6); 3.8981 (0.5); 3.7577 (0.3); 3.5061(0.3); 3.4314 (0.4); 3.3908 (0.6); 3.3244 (853.0); 3.2769 (0.4); 2.6758(4.7); 2.6713 (6.6); 2.6668 (4.9); 2.6623 (2.4); 2.5417 (36.6); 2.5248(20.7); 2.5200 (32.3); 2.5113 (397.7); 2.5069 (800.2); 2.5024 (1050.5);2.4978 (774.7); 2.4933 (385.9); 2.4290 (0.4); 2.3383 (2.1); 2.3338(4.6); 2.3292 415.0 (6.4); 2.3246 (4.7); 2.3201 (2.3); 2.0733 (4.3);1.6153 (13.1); 1.5980 (13.1); 1.4683 (0.8); 1.4514 (0.8); 1.2347 (0.4);0.0081 (1.5); −0.0001 (47.6); −0.0083 (1.8) I-105

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 8.9981 (3.1); 8.8512 (13.7); 8.8507(13.8); 8.7343 (3.6); 8.7158 (3.7); 8.3124 (2.4); 8.1585 (4.1); 8.0898(14.6); 7.8700 (0.6); 7.8612 (6.1); 7.8556 (2.2); 7.8494 (6.6); 7.8439(3.7); 7.8383 (7.0); 7.8322 (2.3); 7.8265 (6.6); 7.8175 (0.6); 7.6419(2.0); 7.3916 (0.6); 7.3826 (6.8); 7.3770 (2.0); 7.3704 (1.0); 7.3606(10.0); 7.3507 (0.8); 7.3442 (1.9); 7.3385 (6.2); 7.3296 (0.5); 6.0234(0.5); 6.0058 (2.4); 5.9880 (3.6); 5.9701 (2.4); 5.9526 (0.5); 3.3305(308.5); 2.6811 (0.8); 2.6766 (1.8); 2.6719 (2.5); 2.6673 (1.8); 2.6628(0.8); 2.5423 (26.8); 2.5255 (7.8); 2.5208 (11.7); 2.5121 (146.8);2.5076 (298.0); 2.5030 (391.0); 2.4983 (281.8); 2.4938 (135.3); 2.3389(0.8); 2.3344 (1.7); 2.3298 (2.4); 2.3252 (1.7); 2.3207 (0.8); 2.0736(4.6); 1.6312 (16.0); 1.6138 (16.0); 0.0081 (0.7); −0.0001 (23.1);−0.0084 (0.7) 379.1 I-106

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.0465 (0.8); 9.0445 (0.8); 9.0196(16.0); 9.0074 (14.6); 8.8039 (2.0); 8.7847 (2.1); 8.3118 (2.7); 8.1836(10.6); 7.8314 (3.6); 7.8299 (3.6); 7.8062 (4.5); 7.7828 (0.8); 7.6520(3.8); 7.6398 (7.2); 7.6277 (3.6); 7.3708 (3.5); 7.3663 (3.3); 7.3571(0.8); 7.3526 (0.9); 7.3471 (3.1); 7.3427 (3.0); 7.3336 (0.6); 7.3290(0.6); 7.0355 (7.2); 7.0336 (7.1); 6.9113 (1.4); 6.9094 (1.4); 6.0925(0.4); 6.0753 (1.7); 6.0573 (2.3); 6.0392 (1.7); 6.0216 (0.4); 3.3256(431.0); 3.3022 (0.8); 3.1997 (5.2); 3.0261 (4.7); 2.6809 (1.0); 2.6765(2.3); 2.6719 (3.2); 2.6673 (2.2); 2.6627 (1.0); 2.5422 (44.6); 2.5254(10.0); 2.5207 (14.7); 2.5120 (185.8); 2.5075 (375.1); 2.5029 (491.4);2.4982 (.352.5); 2.4937 (167.6); 2.3389 (1.0); 2.3343 (2.2); 2.3297(3.1); 2.3251 369.0 (2.2); 2.3205 (1.0); 2.0733 (2.0); 1.6192 (11.2);1.6020 (11.2); 0.0080 (0.7); −0.0002 (24.9); −0.0085 (0.7) I-107

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.1559 (1.8); 9.1377 (1.8); 8.9985(1.6); 8.9861 (16.0); 8.9739 (14.7); 8.3118 (1.5); 8.1514 (10.6); 8.1184(1.0); 7.6526 (0.4); 7.6403 (4.6); 7.6281 (7.8); 7.6160 (3.8); 6.6128(1.1); 6.4133 (11.3); 6.3842 (0.4); 5.9913 (0.4); 5.9739 (1.8); 5.9562(2.8); 5.9384 (1.8); 5.9209 (0.4); 4.4477 (0.3); 4.4404 (0.3); 4.4365(0.4); 4.4320 (0.3); 4.4249 (0.3); 4.2188 (0.7); 3.8808 (0.8); 3.8713(0.8); 3.7242 (0.4); 3.7129 (0.5); 3.7018 (0.5); 3.3259 (228.4); 3.0462(1.7); 2.9849 (1.5); 2.6810 (0.5); 2.6765 (1.0); 2.6719 (1.5); 2.6674(1.1); 2.6628 (0.5); 2.5422 (32.8); 2.5255 (4.5); 2.5208 (6.8); 2.5121(90.4); 2.5076 (184.3); 2.5029 (242.9); 2.4983 (175.3); 2.4938 (84.2);2.3390 (0.5); 2.3344 (1.1); 2.3298 (1.6); 2.3252 (1.1); 2.3207 (0.5);2.1911 326.1 (0.7); 2.1784 (1.3); 2.1697 (1.3); 2.1663 (0.9); 2.1573(2.4); 2.1485 (0.8); 2.1449 (1.4); 2.1362 (1.2); 2.1238 (0.6); 2.0733(1.3); 1.5922 (11.3); 1.5749 (11.3); 1.4867 (1.2); 1.4695 (1.1); 1.1181(0.4); 1.1120 (0.5); 1.1025 (1.5); 1.0973 (0.7); 1.0913 (4.0); 1.0849(4.4); 1.0818 (2.2); 1.0747 (2.0); 1.0703 (3.9); 1.0637 (3.9); 1.0538(1.6); 0.9627 (0.4); 0.9530 (0.6); 0.9474 (0.5); 0.9405 (0.5); 0.9349(0.6); 0.9107 (1.8); 0.9009 (4.3); 0.8945 (4.1); 0.8885 (4.1); 0.8822(4.4); 0.8711 (1.2); −0.0001 (10.3 ) I-108

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.1565 (1.6); 9.1382 (1.6); 9.0017(3.3); 8.9896 (3.3); 8.3448 (2.9); 8.3124 (2.4); 8.1581 (4.8); 7.9856(1.4); 7.9637 (2.6); 7.9471 (2.9); 7.9256 (2.9); 7.8269 (2.2); 7.8226(2.2); 7.8054 (1.6); 7.8011 (1.6); 7.6324 (1.2); 7.6266 (1.0); 7.6205(2.4); 7.6093 (2.7); 7.6056 (2.1); 7.5975 (1.9); 7.5917 (3.5); 7.5857(1.8); 7.5780 (1.5); 7.5740 (1.6); 7.5610 (0.6); 7.5571 (0.4); 6.0555(1.2); 6.0378 (1.9); 6.0201 (1.2); 3.3386 (472.4); 2.6805 (1.0); 2.6761(2.1); 2.6715 (3.0); 2.6669 (2.2); 2.6625 (1.0); 2.5419 (27.9); 2.5250(9.4); 2.5203 (13.9); 2.5116 (174.0); 2.5071 (354.3); 2.5025 (467.2);2.4979 (339.2); 2.4933 (163.9); 2.3385 (0.9); 2.3339 (2.0); 2.3293(2.9); 2.3248 (2.1); 345.1 2.3202 (0.9); 2.0733 (16.0); 1.6788 (7.6);1.6614 (7.6); −0.0001 (10.6) I-109

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 8.8557 (1.7); 8.8375 (1.7); 8.8156(10.6); 8.8140 (10.4); 8.3157 (0.4); 8.1147 (7.9); 7.9845 (5.2); 7.9801(5.3); 7.4313 (5.4); 7.4270 (5.3); 5.9010 (0.3); 5.8835 (1.4); 5.8658(2.1); 5.8481 (1.4); 3.3229 (52.7); 2.6755 (0.8); 2.6709 (1.1); 2.6664(0.8); 2.6618 (0.4); 2.5244 (3.3); 2.5197 (5.0); 2.5110 (61.6); 2.5065(125.2); 2.5020 (165.4); 2.4974 (119.9); 2.4929 (57.9); 2.3433 (16.0);2.3288 (1.2); 2.3243 (0.8); 1.5892 (8.5); 1.5717 (8.5); 1.258.3 (0.3);−0.0002 (5.8) 349.1 I-110

¹H-NMR (600.4 MHz, d₆-DMSO): δ = 9.5461 (2.0); 9.5348 (2.1); 9.1065(3.0); 9.1038 (3.0); 8.6355 (2.0); 8.6318 (2.0); 8.6212 (2.2); 8.6176(2.1); 8.2477 (4.3); 8.2454 (2.6); 8.1548 (8.6); 8.1525 (8.1); 8.1272(3.1); 8.1131 (2.9); 6.0723 (1.4); 6.0609 (2.1); 6.0494 (1.4); 3.4620(0.4); 3.3911 (1067.5); 3.3301 (1.6); 3.3144 (20.3); 3.2964 (0.4);2.6221 (0.4); 2.6193 (0.6); 2.6163 (0.4); 2.5280 (1.1); 2.5250 (1.4);2.5220 (1.4); 2.5101 (67.0); 2.5072 (90.9); 2.5043 (68.6); 2.3941 (0.4);2.3911 (0.6); 2.3881 (0.4); 2.0880 (1.6); 1.6929 (7.4); 1.6813 (7.4);1.3977 (16.0); 1.2454 (0.6); 1.2343 (0.7); 1.2299 (0.7); 1.2186 (0.6);−0.0001 (4.4) 499.0 I-111

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.3280 (1.9); 9.3098 (2.0); 9.0047(11.5); 8.9981 (5.1); 8.9926 (16.0); 8.8504 (4.8); 8.8453 (4.9); 8.3510(2.5); 8.3456 (4.6); 8.3402 (2.5); 8.1785 (9.0); 7.8658 (0.3); 7.8579(3.2); 7.8527 (1.4); 7.8445 (3.5); 7.8358 (3.8); 7.8278 (1.4); 7.8224(3.4); 7.8146 (0.4); 7.6444 (3.1); 7.6323 (5.8); 7.6201 (2.9); 7.4081(0.4); 7.4002 (3.5); 7.3950 (1.1); 7.3833 (1.3); 7.3780 (6.6); 7.3728(1.3); 7.3611 (1.0); 7.3559 (3.2); 6.0784 (0.3); 6.0610 (1.5); 6.0433(2.4); 6.0256 (1.5); 6.0081 (0.3); 3.3317 (32.6); 2.5271 (0.9); 2.5223(1.4); 2.5136 (17.3); 2.5092 (35.1); 2.5046 (46.3); 2.5000 (33.6);2.4955 (16.2); 1.6773 (9.2); 1.6599 (9.2); −0.0002 (0.4) 390.2 I-112

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.3415 (3.0); 9.3234 (3.1); 9.0206(7.1); 9.0151 (7.2); 9.0055 (15.9); 8.9934 (16.0); 8.8690 (7.1); 8.8640(7.1); 8.3752 (3.9); 8.3699 (6.8); 8.3645 (3.7); 8.1809 (13.0); 8.1705(0.6); 7.8455 (1.2); 7.8390 (8.8); 7.8342 (3.1); 7.8223 (3.5); 7.8175(10.9); 7.8110 (1.4); 7.6449 (4.3); 7.6327 (8.2); 7.6205 (5.5); 7.6135(11.0); 7.6087 (3.4); 7.5968 (3.1); 7.5921 (9.0); 7.5855 (1.1); 6.0810(0.5); 6.0637 (2.2); 6.0460 (3.4); 6.0284 (2.2); 6.0110 (0.5); 3.3376(62.7); 2.5283 (1.1); 2.5148 (19.9); 2.5105 (38.4); 2.5060 (49.2);2.5015 (35.7); 2.4971 (17.5); 2.0786 (1.1); 1.6799 (13.3); 1.6625(13.2); −0.0002 (0.4) 406.2 I-113

¹H-NMR (600.1 MHz, CD3CN, 260K): δ = 8.8757 (6.0); 8.8730 (6.1); 8.3392(4.0); 8.3355 (4.1); 8.3248 (4.4); 8.3211 (4.6); 8.0923 (6.1); 8.0780(5.4); 8.0694 (0.3); 8.0450 (13.2); 8.0326 (1.0); 7.8205 (2.3); 7.8083(2.3); 7.2612 (8.1); 7.2582 (11.1); 7.2477 (2.4); 7.2438 (2.7); 7.2415(1.9); 6.9945 (2.0); 6.9913 (3.0); 6.9881 (2.0); 6.9776 (2.1); 6.9748(2.6); 6.9714 (1.9); 6.1992 (0.6); 6.1875 (2.5); 6.1757 (3.9); 6.1639(2.6); 6.1522 (0.6); 5.4729 (3.2); 2.3061 (18.1); 1.9867 (3.2); 1.9786(2.0); 1.9744 (2.4); 1.9707 (17.0); 1.9666 (30.8); 1.9625 (44.9); 1.9584(31.9); 1.9542 (17.5); 1.9462 (3.0); 1.9381 (1.7); 1.9323 (1.5); 1.9240(0.7); 1.6684 (0.4); 1.6511 (16.0); 1.6395 (16.0); 1.0435 (1.1); 1.0393(1.4); 1.0355 (5.3); 1.0320 (5.6); 1.0216 (5.3); 1.0181 (5.4); 1.0146(1.5); 377.1 1.0103 (1.1); 0.7667 (0.4); 0.7557 (2.2); 0.7510 (3.5);0.7480 (5.4); 0.7445 (4.7); 0.7399 (5.2); 0.7366 (3.5); 0.7320 (1.7);0.7194 (0.3); −0.0001 (0.8) I-114

¹H-NMR (600.1 MHz, CD3CN, 260K): δ = 8.8502 (3.8); 8.8491 (4.1); 8.8466(4.2); 8.8454 (4.0); 8.2970 (3.4); 8.2933 (3.4); 8.2827 (3.8); 8.2790(3.8); 8.0575 (4.6); 8.0564 (4.7); 8.0432 (4.0); 8.0420 (4.2); 8.0308(0.3); 8.0137 (9.9); 8.0017 (0.3); 7.7519 (6.5); 7.7491 (6.8); 7.5521(1.1); 7.5404 (1.2); 7.2794 (0.3); 7.2747 (6.6); 7.2718 (6.7); 6.1640(0.5); 6.1523 (2.2); 6.1404 (3.2); 6.1285 (2.2); 6.1168 (0.6); 5.4470(7.6); 2.1654 (0.7); 1.9666 (0.6); 1.9586 (0.3); 1.9544 (0.4); 1.9506(3.2); 1.9465 (6.0); 1.9424 (8.8); 1.9383 (6.1); 1.9341 (3.2); 1.6302(0.7); 1.6282 (0.7); 1.6215 (15.8); 1.6100 (16.0) 359.0 I-115

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.1428 (2.6); 9.1245 (2.7); 8.9973(15.7); 8.9852 (16.0); 8.9342 (0.4); 8.9221 (0.4); 8.1574 (12.7); 8.0285(3.2); 8.0245 (5.5); 8.0206 (3.3); 7.8737 (0.3); 7.8513 (1.0); 7.8439(8.8); 7.8387 (2.9); 7.8274 (5.1); 7.8219 (10.5); 7.8132 (2.8); 7.8092(3.0); 7.7600 (2.7); 7.7436 (2.4); 7.7402 (3.2); 7.6363 (4.2); 7.6241(8.1); 7.6120 (4.2); 7.6060 (0.4); 7.5841 (0.3); 7.5484 (3.2); 7.5290(5.6); 7.5091 (3.9); 7.5033 (5.8); 7.4831 (5.1); 6.0543 (0.4); 6.0370(2.0); 6.0193 (3.2); 6.0015 (2.0); 5.9840 (0.4); 3.3252 (52.0); 2.8912(0.4); 2.7322 (0.3); 2.6760 (0.7); 2.6715 (0.9); 2.6669 (0.7); 2.5250(2.4); 2.5202 (3.5); 2.5115 (53.8); 2.5071 (110.6); 2.5025 (146.3);2.4979 (104.4); 2.4934 (49.0); 2.3340 (0.6); 2.3294 (0.9); 2.3248 (0.7);1.6628 (12.6); 1.6454 (12.7); 1.6244 (0.4); 1.3975 (12.6); 0.1459 (1.5);0.0253 (0.4); 0.0079 (11.7); −0.0002 (327.4); −0.0086 (11.3); −0.0205(0.4); −0.1496 (1.5) 455.3 I-116

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.3383 (2.8); 9.3201 (2.9); 9.0324(6.2); 9.0269 (6.4); 9.0084 (15.7); 8.9963 (16.0); 8.8858 (6.4); 8.8807(6.6); 8.3935 (3.6); 8.3881 (6.6); 8.3827 (3.6); 8.2166 (5.6); 8.1807(13.0); 7.9382 (1.0); 7.9308 (8.9); 7.9257 (3.0); 7.9138 (3.5); 7.9089(11.2); 7.9016 (1.2); 7.8945 (1.0); 7.8896 (2.7); 7.6480 (4.2); 7.6359(8.0); 7.6237 (4.1); 7.5482 (5.8); 7.5280 (5.3); 7.3215 (1.5); 7.3022(1.4); 6.0856 (0.4); 6.0684 (2.1); 6.0508 (3.3); 6.0331 (2.2); 6.0156(0.5); 3.3354 (34.8); 2.5288 (0.8); 2.5238 (1.2); 2.5152 (17.5); 2.5108(35.9); 2.5063 (47.5); 2.5017 (34.5); 2.4972 (16.7); 2.0785 (0.8);1.6799 (12.8); 1.6625 (12.8); 0.1460 (0.5); 0.0079 (4.4); −0.0002(112.0); −0.0086 (4.4); −0.1496 (0.5) 456.2 I-117

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.5333 (3.9); 9.5160 (4.0); 9.3760(9.4); 9.3729 (9.8); 9.2583 (9.9); 9.2551 (9.4); 8.3692 (16.0); 8.3118(9.1); 8.3083 (5.6); 8.2244 (5.0); 8.2203 (8.2); 8.2164 (5.3); 8.1614(5.4); 8.1572 (8.4); 8.1529 (4.5); 6.0957 (0.6); 6.0785 (2.7); 6.0612(4.2); 6.0438 (2.7); 6.0269 (0.6); 3.3264 (163.6); 2.6757 (0.6); 2.6714(0.9); 2.6670 (0.6); 2.5245 (2.6); 2.5068 (103.8); 2.5025 (135.6);2.4981 (99.8); 2.3337 (0.6); 2.3293 (0.8); 2.3249 (0.6); 2.0747 (1.4);1.6431 (15.8); 1.6258 (15.7); 0.1458 (1.3); 0.0077 (10.9); −0.0002(257.8); −0.0084 (11.2); −0.1497 (1.3) 432.2 I-118

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.6157 (1.4); 9.5982 (1.4); 8.5829(2.9); 8.5755 (2.9); 8.4795 (2.0); 8.4753 (3.4); 8.4710 (2.3); 8.4100(3.2); 8.4052 (2.7); 8.3989 (2.6); 8.3161 (0.4); 8.1667 (6.7); 8.0525(0.8); 8.0450 (0.8); 8.0302 (1.3); 8.0228 (1.3); 8.0098 (1.1); 8.0023(1.0); 7.9210 (1.7); 7.9112 (1.8); 7.8985 (1.2); 7.8887 (1.2); 5.9630(1.0); 5.9456 (1.6); 5.9281 (1.0); 3.5685 (16.0); 3.3258 (109.9); 2.6807(0.3); 2.6762 (0.6); 2.6714 (0.9); 2.6670 (0.6); 2.5249 (2.6); 2.5115(53.3); 2.5071 (106.8); 2.5025 (139.6); 2.4979 (99.4); 2.4934 (46.6);2.3339 (0.6); 2.3293 (0.8); 2.3249 (0.6); 1.9089 (5.2); 1.6511 (6.4);1.6337 (6.4); 1.2982 (0.5); 1.2588 (0.8); 1.2345 (1.5); 0.1458 (1.4);0.0079 (14.0); −0.0002 (318.4); −0.0086 (11.0); −0.1497 (1.4) 478.1I-119

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.2840 (2.3); 9.2666 (2.4); 9.0658(4.3); 9.0615 (4.1); 9.0604 (4.2); 8.5864 (3.2); 8.5809 (3.2); 8.5650(3.5); 8.5594 (3.5); 8.2418 (11.1); 8.0817 (4.5); 8.0614 (4.0); 8.0601(4.2); 7.8059 (3.2); 7.8017 (5.4); 7.7976 (3.6); 7.7014 (3.4); 7.6974(5.8); 7.6936 (3.4); 7.5266 (3.5); 7.5220 (6.2); 7.5174 (3.2); 6.1008(0.4); 6.0835 (1.8); 6.0662 (2.8); 6.0487 (1.8); 6.0312 (0.4); 5.7561(7.8); 3.3257 (96.8); 2.6759 (0.6); 2.6715 (0.8); 2.6670 (0.6); 2.5249(2.1); 2.5201 (3.2); 2.5115 (44.9); 2.5071 (92.1); 2.5025 (121.9);2.4980 (87.4); 2.4935 (41.4); 2.3339 (0.5); 2.3294 (0.7); 2.3249 (0.5);1.8164 (1.9); 1.8038 (5.5); 1.7963 (5.9); 1.7848 (2.5); 1.7454 (0.3);1.6727 (0.4); 1.6392 (10.7); 1.6347 (4.9); 1.6218 (16.0); 1.6147 (6.4);1.6013 (2.1); 418.3 0.1458 (1.1); 0.0078 (9.0); −0.0002 (245.2); −0.0086(8.7); −0.1497 (1.1) I-120

¹H-NMR (600.1 MHz, CD3CN, 260K): δ = 9.2780 (1.8); 9.2670 (1.9); 8.8779(5.9); 8.8750 (5.8); 8.3608 (4.0); 8.3571 (3.9); 8.3464 (4.4); 8.3427(4.4); 8.0983 (6.1); 8.0839 (5.5); 8.0642 (12.8); 7.2442 (2.0); 7.2413(2.8); 7.2379 (2.1); 7.2281 (2.0); 7.2254 (2.8); 7.2217 (2.0); 7.1775(7.7); 6.9465 (2.1); 6.9438 (2.7); 6.9406 (1.9); 6.9298 (2.2); 6.9271(2.7); 6.9238 (1.9); 6.5544 (0.6); 6.5429 (2.6); 6.5314 (4.0); 6.5199(2.6); 6.5084 (0.6); 2.3029 (7.9); 1.9862 (16.2); 1.9781 (2.3); 1.9740(3.1); 1.9702 (17.5); 1.9662 (31.8); 1.9620 (46.0); 1.9579 (31.7);1.9538 (17.9); 1.9451 (1.8); 1.9391 (1.5); 1.9309 (0.7); 1.7892 (16.0);1.7776 (16.0); 1.2726 (0.4); 1.2573 (0.6); 1.0455 (1.8); 1.0380 (5.3);1.0345 (5.4); 1.0270 (2.7); 1.0241 (5.4); 1.0206 (5.2); 1.0134 (2.0);0.7566 (2.0); 0.7491 393.1 (6.4); 0.7459 (5.6); 0.7411 (5.5); 0.7378(6.5); 0.7301 (1.8); 0.0053 (0.7); −0.0001 (20.8); −0.0056 (0.7) I-121

¹H-NMR (600.1 MHz, CD3CN, 260K): δ = 8.8014 (2.7); 8.3775 (1.4); 8.3743(1.4); 8.3632 (1.6); 8.3601 (1.5); 8.3373 (2.0); 8.2805 (1.2); 8.2661(1.2); 8.1155 (4.4); 8.0807 (2.4); 8.0631 (3.5); 8.0328 (1.6); 7.8978(1.6); 7.8835 (1.5); 6.8608 (1.4); 6.8437 (1.4); 6.6308 (1.4); 6.6152(2.2); 6.5966 (1.0); 6.5400 (0.8); 6.5265 (0.8); 6.4935 (1.8); 6.4223(3.2); 6.3770 (0.5); 6.3654 (1.5); 6.3539 (1.5); 6.3426 (0.5); 6.2014(0.4); 6.1900 (1.1); 6.1785 (1.1); 6.1670 (0.4); 4.0680 (2.3); 4.0561(7.0); 4.0442 (7.0); 4.0323 (2.3); 3.7163 (0.6); 3.7061 (0.7); 3.6927(0.9); 3.6823 (0.9); 3.5524 (0.8); 3.5406 (0.9); 3.5286 (0.7); 3.5170(0.7); 2.8859 (0.4); 2.8736 (0.3); 2.8597 (1.8); 2.8483 (3.3); 2.8394(1.8); 2.8229 (0.4); 2.2975 (49.5); 2.0805 (0.5); 2.0764 (0.9); 2.0723(1.3); 2.0682 (0.9); 2.0641 (0.5); 1.9846 (39.0); 1.9776 (11.2); 1.9733(14.4); 1.9696 (89.0); 1.9655 (158.1); 1.9614 (230.0); 1.9573 (158.4);1.9532 (80.2); 1.9445 (1.2); 1.8867 (0.3); 1.8779 (0.7); 1.8718 (0.9);1.8643 (1.2); 1.8546 (1.2); 1.8505 (1.6); 1.8464 (1.6); 1.8423 (1.3);1.8382 (0.6); 1.8021 (6.1); 1.7905 (6.3); 1.7543 431.1 (4.6); 1.7427(4.7); 1.7327 (1.1); 1.7169 (0.7); 1.2734 (0.4); 1.2611 (0.7); 1.2178(8.0); 1.2059 (16.0); 1.1940 (8.0); 1.1113 (0.6); 1.1000 (0.9); 1.0869(0.7); 1.0762 (0.6); 1.0221 (0.6); 1.0095 (5.4); 0.9957 (5.1); 0.9878(1.1); 0.6355 (2.8); 0.6089 (0.5); 0.6013 (0.6); 0.5962 (0.6); 0.5876(1.0); 0.5792 (1.0); 0.5699 (0.5); 0.5521 (1.4); 0.5448 (1.7); 0.5360(1.2); 0.5136 (0.7); 0.5055 (0.8); 0.4994 (0.8); 0.4908 (0.9); 0.4854(0.9); 0.4770 (0.8); 0.4695 (0.8); 0.4632 (0.6); 0.3493 (0.5); 0.3419(0.7); 0.3336 (0.9); 0.3279 (0.8); 0.3005 (0.8); 0.2947 (0.9); 0.2869(0.7); 0.2794 (0.4); 0.2694 (0.4); 0.2599 (0.5); 0.2532 (0.8); 0.2455(1.0); 0.2386 (0.9); 0.2320 (0.7); 0.2231 (0.5); 0.2166 (0.5); 0.2081(0.8); 0.2007 (0.8); 0.1948 (1.0); 0.1875 (0.7); 0.0967 (0.4); 0.0053(3.2); −0.0001 (100.6); −0.0057 (3.3); −0.1002 (0.5); −0.1642 (0.3);−0.1724 (0.8); −0.1803 (1.1); −0.1881 (1.1); −0.1959 (0.8); −0.2041(0.4); −0.3881 (0.4); −0.3960 (0.8); −0.4037 (1.1); −0.4116 (1.0);−0.4194 (0.7) I-122

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4670 (1.3); 9.4495 (1.4); 9.0410(2.3); 9.0395 (2.4); 9.0354 (2.5); 9.0339 (2.3); 8.5518 (1.8); 8.5461(1.8); 8.5304 (2.0); 8.5247 (2.0); 8.3162 (0.4); 8.2613 (1.8); 8.2576(3.4); 8.2538 (2.1); 8.2308 (6.1); 8.1650 (1.6); 8.1604 (3.0); 8.1564(2.1); 8.1395 (2.3); 8.1352 (3.1); 8.1306 (1.5); 8.0364 (2.5); 8.0351(2.4); 8.0151 (2.3); 8.0136 (2.3); 6.1327 (1.0); 6.1153 (1.5); 6.0978(1.0); 3.9177 (16.0); 3.3236 (42.0); 3.3135 (16.1); 2.6757 (0.5); 2.6711(0.7); 2.6665 (0.5); 2.5247 (1.9); 2.5199 (2.8); 2.5111 (39.1); 2.5067(79.5); 2.5022 (104.8); 2.4976 (75.6); 2.4931 (36.4); 2.3336 (0.5);2.3290 (0.6); 2.3245 (0.5); 1.6621 (5.6); 1.6448 (5.6); 0.1459 (0.8);0.0080 (6.2); −0.0002 (178.7); −0.0085 (6.9); −0.0201 (0.3); −0.1497(0.8) 464.2 I-123

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4556 (1.7); 9.4381 (1.7); 9.0776(2.9); 9.0759 (3.1); 9.0722 (3.1); 9.0704 (2.8); 8.5806 (2.5); 8.5750(2.3); 8.5591 (2.6); 8.5535 (2.6); 8.3394 (3.1); 8.3138 (1.7); 8.2525(7.8); 8.1304 (3.0); 8.0909 (4.4); 8.0892 (5.0); 8.0856 (3.2); 8.0696(3.1); 8.0678 (3.0); 7.8876 (2.6); 7.8822 (1.1); 7.8742 (2.9); 7.8654(3.0); 7.8573 (1.2); 7.8520 (2.7); 7.3872 (2.9); 7.3822 (0.9); 7.3651(5.4); 7.3483 (0.9); 7.3430 (2.6); 6.1499 (1.2); 6.1325 (1.8); 6.1152(1.2); 3.8242 (0.3); 3.3296 (659.1); 2.6806 (0.8); 2.6763 (1.6); 2.6717(2.3); 2.6670 (1.6); 2.6628 (0.8); 2.5621 (0.4); 2.5251 (7.2); 2.5203(11.3); 2.5117 (134.9); 2.5072 (270.4); 2.5027 (353.9); 2.4981 (254.5);2.4936 (120.9); 2.3386 (0.7); 2.3341 (1.6); 2.3295 (2.2); 2.3250 (1.6);2.3205 (0.7); 1.9886 (0.4); 1.6800 (7.0); 1.6625 (7.0); 1.3981 (16.0);1.2359 (2.4); 1.1757 (0.4); 0.8542 (0.5); 0.1459 (2.7); 0.0079 (25.7);−0.0002 (649.7); −0.0086 (24.6); −0.0328 (0.5); −0.1496 (2.8) 481.2I-124

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.1432 (0.4); 9.1252 (0.4); 8.9885(2.2); 8.9763 (2.2); 8.1569 (1.8); 7.6757 (0.6); 7.6719 (1.0); 7.6680(0.7); 7.6337 (0.6); 7.6215 (1.2); 7.6168 (0.7); 7.6122 (1.0); 7.6092(1.1); 7.5473 (0.6); 7.5428 (1.0); 7.5383 (0.5); 5.9629 (0.5); 3.3229(8.5); 2.5245 (0.6); 2.5111 (11.0); 2.5067 (21.5); 2.5022 (27.8); 2.4977(20.4); 2.4934 (10.0); 1.6417 (1.9); 1.6243 (1.9); 1.2708 (16.0); 0.0079(1.6); −0.0002 (37.0); −0.0085 (1.5) 385.2 I-125

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.1484 (0.4); 9.1304 (0.4); 8.9900(2.5); 8.9778 (2.6); 8.1583 (2.0); 7.7544 (0.6); 7.7503 (1.0); 7.7462(0.7); 7.7141 (0.6); 7.7100 (1.1); 7.7061 (0.6); 7.6711 (0.7); 7.6667(1.1); 7.6623 (0.5); 7.6355 (0.7); 7.6233 (1.3); 7.6112 (0.7); 5.9620(0.5); 3.3275 (1.7); 2.5127 (3.8); 2.5082 (7.7); 2.5036 (10.1); 2.4990(7.3); 2.4945 (3.5); 2.0760 (3.5); 1.6414 (1.9); 1.6240 (1.9); 1.2668(16.0); 0.0079 (0.8); −0.0002 (19.4); −0.0086 (0.7) 431.2 I-126

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 13.6217 (1.4); 9.4748 (3.7); 9.4572(3.8); 9.0148 (6.6); 9.0105 (6.6); 8.5268 (4.5); 8.5212 (4.3); 8.5055(4.8); 8.4999 (4.8); 8.2759 (5.2); 8.2723 (9.1); 8.2686 (5.4); 8.2207(16.0); 8.1685 (4.6); 8.1641 (8.0); 8.1602 (5.6); 8.1391 (5.9); 8.1349(8.2); 8.1305 (4.1); 8.0145 (6.5); 7.993.3 (6.0); 6.1559 (0.6); 6.1385(2.5); 6.1211 (3.9); 6.1037 (2.5); 6.0862 (0.5); 3.3272 (9.9); 3.3161(42.0); 2.6771 (0.6); 2.6725 (0.7); 2.6679 (0.6); 2.5258 (2.7); 2.5123(47.5); 2.5080 (92.8); 2.5035 (119.9); 2.4990 (87.6); 2.4947 (43.4);2.3348 (0.5); 2.3304 (0.7); 2.3258 (0.5); 1.6628 (14.5); 1.6455 (14.4);0.1459 (0.5); 0.0078 (5.0); −0.0002 (118.3); −0.0085 (5.0); −0.1496(0.6) 450.2 I-127

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 10.0999 (1.8); 9.7311 (0.5); 9.5257(2.4); 9.5085 (2.4); 9.3731 (4.7); 9.3720 (4.9); 9.3663 (5.0); 9.3651(4.7); 8.9482 (2.4); 8.9422 (2.4); 8.8570 (3.9); 8.8501 (3.7); 8.8344(4.1); 8.8275 (4.0); 8.3159 (0.5); 8.2891 (4.0); 8.2843 (15.6); 8.2747(1.3); 8.2678 (1.1); 8.2513 (1.1); 8.2444 (1.0); 8.2127 (3.6); 8.2081(5.5); 8.2040 (3.8); 8.1616 (5.2); 8.1605 (5.2); 8.1514 (4.1); 8.1470(6.0); 8.1424 (3.6); 8.1392 (5.2); 8.1379 (5.0); 6.6498 (0.6); 6.6265(0.6); 6.1755 (0.4); 6.1586 (1.8); 6.1413 (2.8); 6.1239 (1.8); 6.1065(0.4); 3.3450 (0.8); 3.3259 (118.8); 3.3196 (32.7); 2.6805 (0.4); 2.6760(0.7); 2.6714 (1.0); 2.6668 (0.8); 2.6622 (0.3); 2.5250 (2.8); 2.5202(4.2); 2.5116 (60.9); 2.5071 (124.5); 2.5025 (163.9); 2.4979 (115.6);2.4933 (53.5); 451.1 2.3384 (0.3); 2.3338 (0.7); 2.3293 (1.0); 2.3247(0.7); 2.0750 (2.5); 1.9891 (0.9); 1.9423 (16.0); 1.8323 (0.5); 1.6721(10.8); 1.6547 (10.7); 1.1752 (0.5); 0.1460 (0.5); 0.0081 (4.3); −0.0001(130.8); −0.0085 (3.9); −0.1495 (0.5) I-128

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4780 (3.3); 9.4603 (3.4); 9.1970(1.6); 9.1825 (3.3); 9.1678 (1.6); 9.0037 (5.9); 8.9993 (5.8); 8.9979(5.7); 8.5027 (4.1); 8.4968 (3.9); 8.4813 (4.4); 8.4754 (4.5); 8.3163(0.5); 8.2842 (4.8); 8.2804 (9.2); 8.2766 (5.5); 8.2137 (16.0); 8.1930(0.5); 8.1828 (4.6); 8.1782 (7.7); 8.1742 (5.4); 8.1379 (5.6); 8.1335(8.2); 8.1291 (4.4); 8.0135 (6.1); 7.9920 (5.7); 6.3021 (0.7); 6.2924(1.4); 6.2826 (0.6); 6.1627 (1.5); 6.1529 (3.4); 6.1432 (1.6); 6.1323(2.4); 6.1149 (3.7); 6.0974 (2.4); 6.0799 (0.5); 6.0232 (0.7); 6.0134(1.6); 6.0037 (0.7); 3.7789 (1.0); 3.7689 (1.3); 3.7644 (1.2); 3.7544(1.1); 3.7399 (2.2); 3.7299 (2.6); 3.7254 (2.5); 3.7154 (2.1); 3.7008(1.2); 3.6906 (1.3); 3.6861 (1.3); 3.6762 (1.0); 3.3248 (43.5); 3.3145(40.6); 2.6807 (0.4); 2.6761 (0.8); 2.6716 (1.1); 2.6671 (0.8); 2.6624(0.4); 2.5251 (2.9); 2.5203 (4.6); 2.5117 (62.9); 2.5072 (128.2); 2.5026(169.0); 2.4981 (121.4); 2.4935 (58.1); 2.3385 (0.4); 2.3340 (0.8);2.3295 (1.1); 2.3249 (0.8); 2.3202 (0.4); 2.0752 (6.6); 1.6635 (13.5);1.6461 (13.5); 1.2344 (1.4); 0.1459 (0.9); 0.0080 (8.0); −0.0001(227.2); −0.0085 (8.0); −0.1496 (0.9) 513.2 I-129

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4741 (3.6); 9.4563 (3.7); 8.9431(6.3); 8.9386 (6.3); 8.7435 (3.8); 8.7334 (3.7); 8.4389 (4.2); 8.4331(3.9); 8.4176 (4.5); 8.4117 (4.4); 8.3162 (0.8); 8.2811 (5.2); 8.2774(9.3); 8.2737 (5.5); 8.1994 (16.0); 8.1808 (4.9); 8.1763 (7.9); 8.1723(5.4); 8.1382 (5.8); 8.1340 (8.4); 8.1295 (4.3); 7.9695 (6.5); 7.9482(6.0); 6.1333 (0.6); 6.1164 (2.5); 6.0989 (3.9); 6.0814 (2.5); 6.0645(0.6); 5.7564 (3.1); 3.3248 (173.5); 3.3166 (44.6); 2.9154 (0.6); 2.9056(1.3); 2.8960 (1.8); 2.8875 (2.8); 2.8775 (2.7); 2.8691 (1.7); 2.8595(1.2); 2.8494 (0.5); 2.7325 (0.4); 2.6897 (0.5); 2.6758 (1.6); 2.6712(2.1); 2.6668 (1.6); 2.6623 (0.8); 2.5247 (7.0); 2.5197 (10.7); 2.5112(128.1); 2.5068 (253.4); 2.5023 (328.3); 2.4978 (235.8); 2.4934 (113.1);2.3336 (1.5); 2.3291 (2.0); 2.3245 (1.5); 1.6556 (14.8); 1.6383 (14.7);0.7565 (1.5); 0.7435 (4.2); 0.7384 (6.2); 0.7264 (5.6); 0.7201 (4.8);0.7090 (2.1); 0.6502 (0.4); 0.6210 (2.2); 0.6106 (6.5); 0.6034 (5.6);0.5950 (4.6); 0.5825 (1.4); 0.1460 (1.9); 0.0080 (16.4); −0.0001(432.7); −0.0085 (15.9); −0.1495 (1.9) 489.2 I-130

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.6151 (8.0); 9.4761 (3.7); 9.4584(3.8); 8.9702 (6.4); 8.9656 (6.4); 8.4736 (4.2); 8.4678 (4.0); 8.4522(4.6); 8.4464 (4.5); 8.3163 (0.6); 8.2749 (5.2); 8.2712 (9.4); 8.2675(5.6); 8.2170 (16.0); 8.1773 (4.9); 8.1728 (8.0); 8.1688 (5.4); 8.1381(5.8); 8.1339 (8.3); 8.1294 (4.3); 8.0147 (6.6); 7.9934 (6.0); 6.1420(0.6); 6.1249 (2.5); 6.1075 (4.0); 6.0899 (2.5); 6.0726 (0.5); 5.7564(3.0); 3.3270 (157.4); 3.3149 (42.2); 2.8911 (1.7); 2.7320 (1.4); 2.6897(0.6); 2.6758 (1.3); 2.6714 (1.8); 2.6669 (1.3); 2.5247 (6.2); 2.5112(107.6); 2.5069 (212.8); 2.5024 (276.4); 2.4978 (199.5); 2.4934 (96.3);2.3337 (1.2); 2.3292 (1.7); 2.3246 (1.2); 1.6578 (14.5); 1.6404 (14.4);1.6181 (3.2); 1.6039 (7.3); 1.5968 (7.9); 1.5840 (3.4); 1.5439 (0.3);1.3853 (0.3); 1.3456 (3.6); 1.3323 (7.4); 1.3255 (7.8); 1.3110 (2.8);1.2735 (0.4); 1.2593 (0.4); 1.2437 (0.4); 0.1459 (1.5); 0.0079 (13.3);−0.0002 (347.3); −0.0085 (13.7); −0.1496 (1.5) 514.2 I-131

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4818 (3.1); 9.4641 (3.2); 9.4414(1.6); 9.4259 (3.2); 9.4101 (1.5); 9.0236 (5.1); 9.0223 (5.3); 9.0179(5.4); 9.0164 (5.0); 8.5233 (3.7); 8.5174 (3.5); 8.5019 (4.0); 8.4960(4.0); 8.3163 (0.5); 8.2872 (4.5); 8.2834 (8.4); 8.2796 (4.9); 8.2186(14.4); 8.1789 (4.3); 8.1743 (6.8); 8.1703 (4.8); 8.1371 (5.3); 8.1328(7.3); 8.1283 (4.0); 8.0275 (5.5); 8.0262 (5.4); 8.0062 (5.1); 8.0047(5.1); 6.1532 (0.4); 6.1360 (2.1); 6.1185 (3.3); 6.1010 (2.1); 6.0834(0.5); 4.1965 (0.8); 4.1723 (2.7); 4.1564 (2.7); 4.1481 (2.9); 4.1322(2.6); 4.1239 (1.1); 4.1079 (0.9); 3.3250 (36.1); 3.3137 (36.4); 2.6764(0.6); 2.6719 (0.9); 2.6673 (0.7); 2.5253 (2.6); 2.5205 (4.1); 2.5119(53.2); 2.5074 (107.0); 2.5029 (139.4); 2.4983 (99.4); 2.4938 (46.9);2.3342 (0.6); 2.3297 (0.8); 2.3252 (0.6); 2.1376 (0.4); 2.0753 (16.0);1.6662 (12.1); 1.6489 (12.1); 0.1459 (0.8); 0.0080 (6.9); −0.0002(188.1); −0.0086 (6.5); −0.1496 (0.8) 531.2 I-132

¹H-NMR (400.2 MHz, CD3CN): δ = 8.2913 (0.7); 8.0657 (2.3); 7.9058 (0.3);6.6244 (0.5); 6.5930 (0.6); 6.5843 (0.6); 6.5124 (0.9); 3.7774 (0.6);3.7733 (0.6); 2.1414 (21.2); 2.1134 (0.3); 2.1073 (0.5); 1.9643 (7.2);1.9579 (2.2); 1.9524 (24.3); 1.9462 (46.4); 1.9400 (65.3); 1.9338(44.6); 1.9277 (22.7); 1.9150 (0.4); 1.7809 (0.4); 1.7746 (0.5); 1.7685(0.6); 1.7624 (0.6); 1.7559 (0.5); 1.7212 (16.0); 1.7037 (15.9); 1.3856(0.4); 1.3219 (0.4); 1.3155 (0.3); 1.2689 (0.8); 1.1735 (1.0); 0.9913(3.5); 0.9704 (3.2); 0.6296 (1.0); 0.6249 (1.0); 0.5947 (0.9); 0.1458(1.1); 0.0191 (0.4); 0.0160 (0.4); 0.0079 (9.8); −0.0002 (245.8);−0.0086 (9.7); −0.1496 (1.1) 405.3 I-133

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.3582 (2.2); 9.3400 (2.1); 8.2660(3.1); 8.2625 (5.1); 8.2590 (3.3); 8.1475 (2.6); 8.1431 (4.8); 8.1393(3.7); 8.1283 (3.8); 8.1242 (5.0); 8.1199 (2.5); 8.0225 (0.6); 8.0113(8.3); 7.8022 (3.9); 7.7954 (3.8); 7.4132 (3.4); 7.3916 (4.0); 7.1311(2.5); 7.1241 (2.4); 7.1095 (2.2); 7.1025 (2.1); 5.8060 (0.4); 5.7886(1.5); 5.7708 (2.2); 5.7531 (1.4); 5.7355 (0.4); 5.6754 (7.2); 4.0560(1.2); 4.0382 (3.8); 4.0205 (3.8); 4.0027 (1.3); 3.3285 (23.1); 3.3181(23.0); 2.5075 (41.3); 2.5031 (53.6); 2.4988 (40.4); 2.3299 (0.4);1.9895 (16.0); 1.9632 (0.3); 1.9435 (1.5); 1.9099 (0.7); 1.8331 (0.5);1.8299 (0.5); 1.7863 (0.4); 1.6015 (0.7); 1.5833 (8.7); 1.5659 (8.3);1.3363 (0.4); 1.2498 (0.3); 1.2352 (0.5); 1.1931 (4.4); 1.1753 (8.5);1.1653 (0.7); 421.2 1.1575 (4.4); 1.1467 (0.5); 1.1306 (0.3); −0.0002(3.6) I-134

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4596 (3.4); 9.4419 (3.3); 8.6991(3.4); 8.3162 (0.4); 8.2840 (6.6); 8.2187 (2.7); 8.1957 (16.0); 8.1343(6.4); 7.9164 (4.9); 7.8955 (4.2); 6.1370 (1.9); 6.1196 (2.8); 6.1023(1.8); 6.0869 (0.6); 5.7565 (4.0); 3.3233 (49.8); 3.3172 (33.0); 3.0083(7.7); 2.8915 (0.4); 2.6712 (1.5); 2.5023 (198.0); 2.3296 (1.3); 1.6506(11.6); 1.6335 (11.3); 0.5125 (2.4); 0.4115 (2.7); 0.1458 (0.7); −0.0002(124.3); −0.1499 (0.7) 503.2 I-135

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4710 (2.5); 9.4533 (2.6); 8.9556(4.7); 8.9501 (4.7); 8.7556 (1.9); 8.7442 (1.9); 8.4506 (2.8); 8.4448(2.7); 8.4293 (3.0); 8.4235 (3.0); 8.2772 (6.2); 8.2739 (3.9); 8.2013(10.3); 8.1928 (0.6); 8.1799 (3.2); 8.1759 (5.6); 8.1722 (3.8); 8.1364(3.7); 8.1326 (5.6); 7.9791 (4.8); 7.9578 (4.5); 6.1371 (0.4); 6.1199(1.8); 6.1025 (2.9); 6.0850 (1.9); 6.0671 (0.4); 3.3269 (92.6); 3.3154(28.6); 3.0150 (0.3); 2.9126 (0.4); 2.8913 (0.6); 2.8314 (12.6); 2.8201(12.6); 2.7316 (0.4); 2.6900 (1.1); 2.6761 (0.6); 2.6715 (0.9); 2.6672(0.6); 2.5247 (2.6); 2.5070 (103.3); 2.5027 (134.6); 2.4982 (98.5);2.3337 (0.6); 2.3295 (0.8); 2.3252 (0.6); 2.0750 (16.0); 1.6593 (10.7);1.6419 (10.7); 0.1457 (0.7); 0.0077 (5.0); −0.0002 (143.5); −0.0085(5.5); −0.1498 (0.7) 463.1 I-136

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.5184 (1.7); 9.5009 (1.9); 9.4910(16.0); 8.9765 (0.4); 8.2928 (2.1); 8.2892 (4.0); 8.2856 (2.6); 8.2719(7.1); 8.2172 (2.1); 8.2128 (3.6); 8.2090 (2.4); 8.1555 (2.3); 8.1511(3.7); 8.1469 (2.1); 6.0988 (1.1); 6.0814 (1.8); 6.0642 (1.2); 3.3551(0.4); 3.3457 (0.3); 3.3252 (52.5); 3.2744 (1.1); 2.6754 (0.4); 2.6709(0.5); 2.6664 (0.4); 2.5239 (1.5); 2.5064 (63.3); 2.5019 (83.6); 2.4975(62.2); 2.3330 (0.4); 2.3288 (0.5); 2.3244 (0.4); 2.0756 (0.9); 1.6527(6.6); 1.6353 (6.6); −0.0002 (9.5); −0.0084 (0.3) 432.0 I-137

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4850 (3.4); 9.4675 (3.6); 9.0375(5.3); 9.0361 (5.7); 9.0318 (5.7); 9.0302 (5.5); 9.0159 (1.0); 9.0142(1.0); 9.0104 (1.0); 9.0086 (1.0); 9.0012 (0.8); 8.9971 (0.7); 8.9952(0.7); 8.5512 (4.2); 8.5453 (3.8); 8.5297 (4.6); 8.5238 (4.6); 8.5057(0.8); 8.5001 (0.8); 8.4879 (0.6); 8.4821 (0.5); 8.4666 (0.6); 8.4607(0.6); 8.3160 (1.0); 8.2861 (5.2); 8.2823 (9.4); 8.2785 (5.6); 8.2742(1.3); 8.2703 (1.6); 8.2664 (1.0); 8.2546 (0.4); 8.2271 (15.2); 8.2206(2.8); 8.2016 (2.2); 8.1931 (4.6); 8.1885 (7.4); 8.1845 (5.7); 8.1798(1.4); 8.1755 (0.8); 8.1673 (0.8); 8.1625 (1.2); 8.1586 (0.9); 8.1419(5.5); 8.1376 (8.9); 8.1331 (6.1); 8.0207 (5.3); 8.0159 (1.4); 7.9991(5.0); 7.9947 (1.3); 7.9780 (0.8); 7.9567 (0.8); 7.7105 (0.4); 6.1552(0.5); 6.1377 (2.6); 6.1202 (4.1); 6.1128 (0.9); 6.1028 (2.6); 6.0853(0.6); 3.4895 (0.4); 3.3645 (23.2); 3.3347 (14.4); 3.3178 (49.7); 3.2524(1.6); 3.1416 (0.4); 3.0247 (1.1); 2.8907 (0.4); 2.6897 (0.6); 2.6803(0.7); 2.6757 (1.5); 2.6711 (2.1); 2.6666 (1.5); 2.6620 (0.7); 2.5971(0.5); 2.5247 (5.6); 2.5200 (8.8); 2.5113 527.2 (123.2); 2.5068 (252.7);2.5022 (334.2); 2.4976 (239.4); 2.4931 (113.6); 2.3382 (0.8); 2.3336(1.6); 2.3290 (2.2); 2.3245 (1.6); 2.3198 (0.8); 2.0747 (3.1); 2.0089(0.4); 1.9897 (0.4); 1.6604 (16.0); 1.6430 (16.0); 1.2725 (1.1); 1.2582(1.6); 1.2424 (2.5); 1.2348 (2.4); 0.8540 (0.6); 0.1459 (1.9); 0.0214(0.5); 0.0207 (0.5); 0.0177 (0.8); 0.0147 (1.0); 0.0080 (17.9); −0.0002(501.8); −0.0086 (17.2); −0.0245 (0.5); −0.0289 (0.4); −0.1496 (2.0)I-138

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 10.3814 (2.4); 9.3995 (1.4); 9.3816(1.4); 8.6943 (2.4); 8.6884 (2.4); 8.2520 (2.6); 8.2480 (5.4); 8.2443(2.6); 8.2323 (1.6); 8.2258 (1.6); 8.1360 (1.0); 8.1310 (4.2); 8.1278(6.2); 8.1242 (4.2); 8.1193 (1.2); 8.1144 (7.2); 7.7789 (2.8); 7.7569(2.6); 5.9533 (1.0); 5.9358 (1.6); 5.9182 (1.0); 3.3256 (31.5); 3.3131(17.5); 2.6891 (0.4); 2.6756 (0.4); 2.6710 (0.6); 2.6664 (0.4); 2.5246(1.6); 2.5199 (2.3); 2.5112 (34.4); 2.5067 (71.4); 2.5021 (94.5); 2.4975(67.6); 2.4929 (32.2); 2.3335 (0.4); 2.3289 (0.6); 2.3243 (0.4); 2.1049(16.0); 2.0756 (10.9); 1.6310 (5.8); 1.6136 (5.8); 0.0080 (0.4); −0.0002(14.0); −0.0085 (0.4) 463.1 I-139

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 10.6368 (4.7); 9.3984 (2.7); 9.3806(2.8); 8.7140 (5.0); 8.7085 (4.9); 8.7075 (4.9); 8.2611 (3.4); 8.2540(6.5); 8.2499 (8.3); 8.2460 (4.7); 8.2390 (3.7); 8.2324 (3.6); 8.1331(2.0); 8.1281 (8.3); 8.1249 (11.6); 8.1215 (8.4); 8.1154 (15.2); 7.7757(5.3); 7.7534 (4.9); 5.9699 (0.4); 5.9526 (1.9); 5.9351 (3.0); 5.9175(1.9); 5.9000 (0.4); 3.3276 (57.6); 3.3119 (33.8); 2.6761 (0.5); 2.6716(0.7); 2.6669 (0.6); 2.5251 (2.1); 2.5204 (3.0); 2.5117 (43.6); 2.5072(90.5); 2.5026 (119.2); 2.4979 (84.3); 2.4934 (39.3); 2.3339 (0.5);2.3294 (0.7); 2.3248 (0.5); 1.8366 (0.5); 1.8210 (1.6); 1.8059 (2.1);1.7905 (1.7); 1.7748 (0.6); 1.6304 (10.8); 1.6130 (10.8); 0.8659 (9.1);0.8515 (16.0); 0.0080 (0.4); −0.0002 (14.7); −0.0086 (0.4 489.1 I-140

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4392 (1.2); 9.4212 (1.2); 8.6163(2.2); 8.6152 (2.4); 8.6100 (2.4); 8.6087 (2.3); 8.2936 (1.8); 8.2897(3.4); 8.2859 (2.0); 8.1855 (2.8); 8.1823 (3.0); 8.1787 (3.4); 8.1636(2.1); 8.1571 (2.1); 8.1440 (2.1); 8.1397 (3.0); 8.1351 (1.6); 7.8516(2.6); 7.8503 (2.6); 7.8297 (2.3); 7.8283 (2.3); 6.0154 (0.9); 5.9978(1.4); 5.9802 (0.9); 5.7590 (3.7); 3.3256 (30.6); 3.3233 (18.6); 3.3096(0.5); 2.6712 (0.4); 2.5248 (1.1); 2.5201 (1.5); 2.5114 (24.4); 2.5069(51.2); 2.5023 (68.0); 2.4977 (48.8); 2.4931 (23.3); 2.3284 (16.0);1.6176 (5.1); 1.6002 (5.1); −0.0002 (10.6); −0.0086 (0.3) 454.2 I-141

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 10.5968 (5.7); 9.5208 (3.0); 9.5032(3.1); 9.1139 (4.8); 9.1126 (5.1); 9.1082 (5.1); 9.1067 (4.9); 8.5850(3.6); 8.5791 (3.4); 8.5636 (3.8); 8.5577 (3.9); 8.3061 (4.6); 8.3023(8.8); 8.2984 (5.1); 8.2811 (0.4); 8.2287 (16.0); 8.2117 (4.6); 8.2070(7.0); 8.2030 (4.9); 8.1919 (0.7); 8.1802 (0.4); 8.1469 (5.4); 8.1425(7.7); 8.1380 (4.5); 8.1292 (0.5); 8.0580 (5.4); 8.0566 (5.5); 8.0367(5.2); 8.0352 (5.2); 7.8327 (0.4); 7.8240 (4.3); 7.8185 (1.7); 7.8114(4.8); 7.8063 (2.7); 7.8011 (5.1); 7.7941 (1.8); 7.7885 (4.8); 7.7797(0.4); 7.2664 (0.5); 7.2577 (5.5); 7.2520 (1.6); 7.2448 (0.8); 7.2403(1.9); 7.2354 (8.8); 7.2305 (1.9); 7.2260 (0.7); 7.2187 (1.6); 7.2130(5.2); 7.2041 (0.4); 6.1873 (0.5); 6.1697 (2.0); 6.1522 (3.2); 6.1347(2.1); 6.1176 (0.4); 5.7590 (7.4); 3.3264 (140.3); 3.3194 (40.7); 2.6759(1.7); 2.6711 (1.8); 2.6665 (1.2); 2.6620 (0.6); 2.5247 (4.9); 2.5200(7.2); 2.5112 (99.8); 2.5067 (206.6); 2.5021 (272.6); 2.4975 (193.4);2.4929 (90.3); 2.3381 (0.5); 2.3336 (1.2); 2.3290 (1.7); 2.3244 (1.2);2.3200 (0.5); 1.6854 (11.8); 1.6679 (12.1); 1.6484 (0.8); 1.2469 (1.5);1.2341 (3.2); 1.2186 (1.1); 1.2059 (0.6); 1.1937 (0.6); 1.1895 (0.6);1.1772 (0.4); 0.8536 (0.6); 0.0081 (1.0); −0.0001 (33.6); −0.0085 (0.9)543.1 I-142

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4897 (1.2); 9.4719 (1.2); 9.0452(2.2); 9.0434 (2.4); 9.0397 (2.4); 9.0379 (2.2); 8.5487 (2.0); 8.5432(1.9); 8.5272 (2.1); 8.5216 (2.1); 8.3165 (1.9); 8.3126 (3.6); 8.3088(2.1); 8.2227 (1.9); 8.2181 (2.8); 8.2141 (1.9); 8.1537 (2.2); 8.1493(3.1); 8.1448 (1.7); 8.0312 (2.5); 8.0293 (2.4); 8.0096 (2.4); 8.0078(2.3); 6.1272 (1.0); 6.1097 (1.5); 6.0921 (1.0); 5.7591 (4.1); 3.9284(0.8); 3.3680 (0.7); 3.3283 (20.2); 3.3265 (19.6); 2.5253 (0.8); 2.5206(1.2); 2.5119 (17.8); 2.5074 (36.4); 2.5028 (47.7); 2.4981 (33.7);2.4936 (15.6); 2.3476 (16.0); 2.3344 (0.4); 2.3296 (0.4); 1.6297 (5.2);1.6123 (5.2); −0.0002 (7.8) 445.2 I-143

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4432 (2.2); 9.4254 (2.2); 8.6009(4.6); 8.5935 (4.7); 8.3163 (1.0); 8.2603 (3.3); 8.2565 (6.5); 8.2527(3.8); 8.1612 (3.4); 8.1574 (16.0); 8.1528 (4.6); 8.1399 (4.5); 8.1356(5.7); 8.1310 (2.7); 8.0624 (1.4); 8.0549 (1.3); 8.0419 (1.8); 8.0401(2.2); 8.0326 (2.1); 8.0197 (2.0); 8.0122 (1.8); 7.9255 (2.7); 7.9158(2.8); 7.9029 (2.0); 7.8934 (2.0); 5.9694 (0.4); 5.9520 (1.7); 5.9346(2.7); 5.9171 (1.7); 5.8993 (0.4); 3.3242 (134.4); 3.3168 (31.5); 2.6799(0.7); 2.6755 (1.6); 2.6709 (2.2); 2.6663 (1.6); 2.6617 (0.8); 2.5244(5.9); 2.5197 (8.5); 2.5110 (125.8); 2.5065 (263.0); 2.5019 (350.4);2.4973 (250.5); 2.4928 (118.1); 2.3378 (0.6); 2.3333 (1.5); 2.3288(2.1); 2.3242 (1.5); 2.3199 (0.7); 1.6385 (10.4); 1.6211 (10.3); 0.0081(1.1); −0.0001 424.1 (38.8); −0.0084 (1.1) I-144

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4557 (3.0); 9.4380 (3.1); 8.6464(5.9); 8.6450 (6.6); 8.6400 (6.6); 8.6385 (6.5); 8.3157 (0.6); 8.2712(4.8); 8.2674 (9.6); 8.2635 (5.6); 8.2212 (5.4); 8.2147 (5.1); 8.1993(6.1); 8.1928 (6.1); 8.1814 (16.0); 8.1656 (4.4); 8.1608 (7.8); 8.1569(6.1); 8.1431 (6.4); 8.1388 (8.0); 8.1342 (4.1); 7.8991 (7.0); 7.8976(7.2); 7.8773 (6.2); 7.8758 (6.5); 6.0297 (0.5); 6.0126 (2.3); 5.9951(3.7); 5.9776 (2.3); 5.9602 (0.5); 4.0381 (0.7); 4.0203 (0.8); 3.3268(171.0); 3.3188 (43.5); 2.6807 (0.4); 2.6762 (0.8); 2.6716 (1.1); 2.6670(0.8); 2.6627 (0.4); 2.5252 (2.8); 2.5205 (4.1); 2.5118 (63.4); 2.5073(133.6); 2.5027 (178.7); 2.4980 (127.4); 2.4935 (59.8); 2.3386 (0.4);2.3341 (0.8); 2.3295 (1.1); 2.3249 (0.8); 2.3206 (0.4); 1.9893 (3.5);440.0 1.6400 (14.0); 1.6226 (13.9); 1.2497 (0.3); 1.2355 (0.5); 1.1932(1.0); 1.1753 (2.0); 1.1576 (1.0); −0.0001 (6.1) I-145

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4051 (1.0); 9.3872 (1.0); 8.2525(3.4); 8.2485 (3.4); 8.2449 (3.5); 8.1356 (5.1); 8.1319 (4.8); 8.0992(4.7); 7.7535 (1.5); 7.7312 (2.5); 7.6681 (1.7); 7.6606 (1.6); 7.6458(1.0); 7.6383 (1.1); 5.8959 (0.7); 5.8784 (1.1); 5.8608 (0.7); 5.7571(0.7); 3.9554 (1.2); 3.8859 (16.0); 3.7314 (0.4); 3.6726 (0.8); 3.3256(7.2); 3.3177 (12.1); 2.5255 (0.5); 2.5208 (0.8); 2.5121 (11.5); 2.5076(24.0); 2.5030 (31.9); 2.4984 (22.8); 2.4939 (10.8); 1.9099 (1.2);1.6265 (4.3); 1.6091 (4.4); −0.0002 (1.1) 436.1 I-146

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.5372 (2.1); 9.5198 (2.1); 9.2270(5.7); 9.2242 (5.6); 9.0386 (5.5); 9.0245 (5.7); 8.3213 (3.4); 8.3175(6.5); 8.3136 (3.7); 8.2775 (10.7); 8.2306 (3.4); 8.2261 (5.1); 8.2220(3.5); 8.1574 (3.7); 8.1530 (5.5); 8.1485 (3.0); 8.0063 (4.0); 8.0032(4.0); 7.9923 (3.9); 7.9892 (3.8); 6.2734 (0.3); 6.2565 (1.6); 6.2391(2.6); 6.2217 (1.6); 6.2044 (0.4); 5.7572 (16.0); 4.0385 (0.9); 4.0207(1.0); 4.0029 (0.3); 3.3277 (42.9); 2.6726 (0.4); 2.5261 (1.1); 2.5213(1.7); 2.5127 (22.8); 2.5082 (46.2); 2.5036 (60.4); 2.4990 (42.2);2.4944 (19.2); 2.3304 (0.4); 2.0762 (6.8); 1.9899 (4.3); 1.9096 (1.4);1.6696 (10.1); 1.6522 (10.0); 1.1934 407.1 (1.2); 1.1756 (2.4); 1.1578(1.2); −0.0002 (2.3) I-147

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.5544 (3.2); 9.5374 (3.3); 8.3386(5.2); 8.3348 (10.0); 8.3310 (5.8); 8.3159 (1.3); 8.2438 (5.2); 8.2391(8.1); 8.2351 (5.4); 8.2086 (16.0); 8.1652 (5.6); 8.1607 (8.4); 8.1563(4.7); 7.8031 (9.3); 7.7943 (14.2); 7.7635 (14.3); 7.7548 (9.2); 6.0950(0.5); 6.0777 (2.6); 6.0605 (4.0); 6.0432 (2.6); 6.0260 (0.5); 4.0376(0.7); 4.0199 (0.7); 3.3316 (46.8); 3.3236 (138.1); 2.6800 (0.9); 2.6755(1.9); 2.6709 (2.6); 2.6663 (1.9); 2.6617 (0.9); 2.5245 (6.8); 2.5197(10.6); 2.5110 (151.8); 2.5065 (314.8); 2.5019 (417.8); 2.4973 (297.9);2.4928 (139.9); 2.3379 (0.8); 2.3334 (1.8); 2.3287 (2.5); 2.3242 (1.8);2.3196 (0.8); 412.1 2.0746 (0.8); 1.9889 (3.1); 1.6407 (15.9); 1.6232(15.9); 1.2495 (0.6); 1.2362 (1.1); 1.1928 (1.0); 1.1750 (1.9); 1.1572(0.9); 0.0080 (0.4); −0.0002 (14.6): −0.0086 (0.4) I-148

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4745 (3.4); 9.4568 (3.4); 8.8182(6.0); 8.8055 (6.1); 8.3245 (8.6); 8.3164 (0.6); 8.2623 (4.8); 8.2586(9.1); 8.2549 (5.3); 8.2405 (16.0); 8.1655 (3.9); 8.1611 (8.0); 8.1571(5.7); 8.1457 (6.0); 8.1415 (8.1); 8.1371 (3.5); 7.9744 (5.0); 7.9712(4.9); 7.9618 (4.8); 7.9585 (4.7); 6.0708 (0.6); 6.0535 (2.6); 6.0361(4.0); 6.0186 (2.6); 6.0016 (0.5); 4.0559 (0.4); 4.0380 (1.4); 4.0203(1.4); 4.0024 (0.5); 3.3259 (86.4); 3.3197 (43.5); 2.6762 (0.8); 2.6716(1.1); 2.6672 (0.8); 2.5250 (2.9); 2.5200 (4.4); 2.5115 (66.5); 2.5071(135.0); 2.5026 (177.0); 2.4981 (125.8); 2.4937 (59.2); 2.3338 (0.8);2.3294 (1.1); 2.3250 (0.8); 431.1 1.9893 (5.8); 1.9037 (0.4); 1.6483(15.2); 1.6309 (15.1); 1.1930 (1.5); 1.1752 (3.1); 1.1574 (1.5); −0.0001(4.5) I-149

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.1942 (0.8); 9.1773 (0.8); 8.3158(0.6); 8.1858 (4.1); 7.7968 (2.4); 7.7880 (3.8); 7.7589 (3.9); 7.7502(2.5); 7.6429 (1.3); 7.6385 (2.0); 7.6342 (1.4); 7.4643 (1.2); 7.4606(2.1); 7.4570 (1.2); 7.3428 (1.2); 7.3383 (2.0); 7.3340 (1.1); 6.0231(0.7); 6.0058 (1.0); 5.9885 (0.7); 3.3255 (222.9); 2.6799 (0.5); 2.6755(1.1); 2.6709 (1.6); 2.6663 (1.1); 2.6618 (0.5); 2.5244 (3.8); 2.5197(5.6); 2.5110 (87.9); 2.5065 (183.4); 2.5019 (243.7); 2.4973 (173.3);2.4928 (81.4); 2.3379 (0.5); 2.3334 (1.1); 2.3288 (1.5); 2.3241 (1.1);2.3198 (0.5); 2.0157 (0.4); 2.0073 (0.4); 1.9948 (0.9); 1.9823 (0.5);1.9741 (0.4); 1.6115 374.2 (4.2); 1.5940 (4.2); 1.3978 (16.0); 1.0229(0.4); 1.0121 (1.4); 1.0064 (1.5); 1.0023 (0.7); 0.9960 (0.7); 0.9910(1.5); 0.9854 (1.5); 0.9752 (0.6); 0.7848 (0.6); 0.7746 (1.5); 0.7722(1.2); 0.7690 (1.4); 0.7620 (1.5); 0.7570 (1.5); 0.7458 (0.5); −0.0002(8.6) I-150

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 11.7091 (2.4); 9.4277 (3.5); 9.4101(3.6); 8.8125 (6.3); 8.8064 (6.2); 8.3573 (4.0); 8.3508 (3.8); 8.3351(4.5); 8.3286 (4.4); 8.3163 (0.5); 8.2525 (4.8); 8.2487 (9.0); 8.2450(5.4); 8.1569 (16.0); 8.1414 (3.5); 8.1367 (8.5); 8.1328 (7.2); 8.1291(7.6); 8.1249 (8.4); 8.1203 (3.2); 7.9125 (6.6); 7.8904 (6.0); 6.0246(0.5); 6.0074 (2.4); 5.9900 (3.7); 5.9725 (2.4); 5.9552 (0.5); 3.3263(91.2); 3.3091 (40.3); 2.6761 (0.9); 2.6716 (1.2); 2.6670 (0.9); 2.6626(0.4); 2.5249 (3.8); 2.5115 (74.2); 2.5071 (147.7); 2.5026 (193.0);2.4981 (138.4); 2.4937 (66.1); 2.3340 (0.9); 2.3295 (1.2); 2.3248 (0.8);2.0752 (0.6); 1.9093 (0.4); 1.6489 (13.8); 1.6315 (13.7); 0.0081 (1.3);−0.0001 (32.7); −0.0084 (1.1) 517.2 I-151

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.3855 (3.0); 9.3674 (3.1); 8.5394(8.2); 8.5332 (8.8); 8.3490 (1.8); 8.3429 (1.6); 8.3280 (2.2); 8.3251(2.3); 8.3220 (2.2); 8.3190 (1.9); 8.3160 (1.3); 8.3042 (1.8); 8.2979(1.6); 8.2270 (16.0); 8.1608 (3.8); 8.1570 (9.0); 8.1532 (6.2); 8.1443(5.8); 8.1396 (8.4); 8.1355 (4.2); 8.0540 (5.3); 8.0495 (7.2); 8.0453(4.5); 5.3864 (0.5); 5.3689 (2.2); 5.3512 (3.5); 5.3335 (2.3); 5.3156(0.5); 3.3274 (280.4); 3.3102 (41.5); 2.6803 (0.6); 2.6758 (1.2); 2.6712(1.6); 2.6666 (1.2); 2.6623 (0.6); 2.5247 (4.2); 2.5200 (6.5); 2.5113(95.0); 2.5068 (197.3); 2.5022 (261.4); 2.4976 (185.2); 2.4931 (86.3);2.3382 (0.5); 2.3337 (1.1); 2.3291 (1.6); 2.3245 (1.1); 2.3200 (0.5);1.6316 (13.8); 1.6140 (13.8); 0.0080 (1.0); −0.0002 (32.8); −0.0085(0.9) 442.2 I-152

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 10.2865 (0.7); 9.4279 (1.0); 9.4100(1.0); 8.3482 (1.7); 8.3468 (1.8); 8.3419 (1.8); 8.3402 (1.7); 8.2709(1.5); 8.2671 (2.8); 8.2632 (1.6); 8.1627 (1.3); 8.1580 (2.3); 8.1540(1.7); 8.1369 (2.0); 8.1298 (5.6); 7.8843 (0.8); 7.8778 (0.6); 7.8623(2.0); 7.8558 (2.0); 7.8372 (2.4); 7.8359 (2.5); 7.8154 (0.9); 7.8138(0.9); 5.9681 (0.7); 5.9505 (1.1); 5.9329 (0.7); 3.3296 (16.5); 3.3174(12.0); 3.0898 (13.0); 2.5260 (0.5); 2.5211 (0.8); 2.5125 (9.9); 2.5080(20.0); 2.5035 (26.0); 2.4989 (18.3); 2.4943 (8.4); 2.0754 (16.0);1.6385 (4.0); 1.6211 (3.9); 1.2345 (0.7); −0.0002 (6.0) 499.2 I-153

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 10.7622 (4.9); 9.4133 (2.5); 9.3955(2.6); 8.6754 (4.2); 8.6691 (4.3); 8.2505 (5.7); 8.2407 (2.5); 8.2341(2.2); 8.2185 (2.5); 8.2120 (2.5); 8.1366 (5.9); 8.1305 (15.8); 7.8362(4.6); 7.8142 (4.2); 5.9936 (0.4); 5.9764 (1.6); 5.9589 (2.6); 5.9413(1.7); 5.9237 (0.4); 3.9942 (16.0); 3.3306 (44.0); 3.3141 (25.4); 2.8312(0.4); 2.6677 (0.7); 2.5075 (53.5); 2.5035 (68.7); 2.4994 (52.2); 2.3305(0.4); 1.6385 (9.5); 1.6211 (9.4); −0.0002 (56.0); −0.0082 (2.3) 488.2I-154

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 10.4380 (5.8); 9.4095 (2.6); 9.3915(2.7); 8.7403 (5.2); 8.7346 (5.0); 8.3159 (0.8); 8.2552 (4.2); 8.2531(4.8); 8.2491 (10.6); 8.2454 (4.7); 8.2333 (3.7); 8.2267 (3.7); 8.1740(0.5); 8.1418 (3.1); 8.1370 (7.0); 8.1318 (16.0); 8.1269 (5.8); 8.1227(6.8); 8.1180 (2.9); 7.9428 (0.3); 7.8204 (5.4); 7.7982 (4.9); 5.9981(0.4); 5.9809 (1.9); 5.9633 (3.0); 5.9457 (1.9); 5.9281 (0.4); 3.3273(257.5); 3.3109 (35.5); 2.6803 (0.8); 2.6758 (1.8); 2.6712 (2.4); 2.6667(1.7); 2.6622 (0.8); 2.5247 (7.2); 2.5200 (10.4); 2.5113 (140.6); 2.5068(288.5); 2.5022 (378.6); 2.4976 (267.2); 2.4931 (124.8); 2.3382 (0.8);2.3336 (1.7); 2.3290 (2.4); 2.3244 (1.7); 2.3199 (0.8); 1.7673 (0.5);1.7467 (3.0); 1.7376 (12.1); 1.7286 (12.1); 1.7195 (3.1); 1.6991 (0.5);1.6343 (11.1); 1.6169 (11.0); 1.2697 (0.4); 1.2179 (0.3); 0.1459 (1.8);0.0080 (14.1); −0.0002 (444.0); −0.0085 (13.8); −0.0208 (0.5); −0.1496(1.8) 514.2 I-155

¹H-NMR (600.1 MHz, CD3CN, 260K): δ = 8.3856 (7.1); 8.3826 (7.4); 8.2804(4.4); 8.2769 (4.2); 8.2661 (4.6); 8.2626 (4.4); 8.0716 (13.7); 7.8681(6.9); 7.8538 (6.4); 6.8546 (8.4); 6.7962 (2.4); 6.6056 (2.3); 6.3773(1.6); 6.3656 (4.8); 6.3539 (4.8); 6.3423 (1.5); 4.7334 (0.5); 4.7175(1.6); 4.7071 (1.1); 4.7015 (1.9); 4.6914 (2.6); 4.6860 (1.0); 4.6754(2.6); 4.6594 (0.9); 4.6129 (0.8); 4.5980 (2.6); 4.58.70 (2.8); 4.5718(2.0); 4.5569 (1.8); 4.5419 (0.6); 4.0681 (1.4); 4.0562 (4.1); 4.0443(4.2); 4.0324 (1.4); 2.3012 (9.1); 2.1187 (0.4); 2.0770 (0.3); 2.0729(0.5); 2.0688 (0.3); 2.0598 (0.4); 1.9848 (20.2); 1.9782 (5.2); 1.9740(5.9); 1.9702 (33.8); 1.9661 (58.8); 1.9620 (86.1); 1.9579 (59.9);1.9538 (30.8); 1.8551 (0.4); 1.8511 (0.5); 1.8469 (0.6); 1.8428 (0.5);1.7483 (15.6); 1.7366 (16.0); 1.7238 (2.1); 1.7158 (2.5); 1.7084 (1.9);1.7026 (1.5); 1.6943 (0.8); 1.2179 (4.8); 1.2060 (9.5); 1.1941 (4.8);1.0343 (0.6); 1.0160 (6.3); 1.0127 (6.6); 1.0021 (6.2); 0.9988 (6.5);0.9809 (0.8); 0.6104 (1.7); 0.6015 (2.2); 0.5949 (2.4); 475.1 0.5712(0.3); 0.5416 (2.1); 0.5364 (2.0); 0.5271 (1.5) I-156

¹H-NMR (600.1 MHz, CD3CN, 260K): δ = 8.7988 (2.1); 8.7962 (2.1); 8.3772(1.3); 8.3736 (1.9); 8.3632 (1.3); 8.3600 (1.3); 8.2681 (0.5); 8.2539(0.6); 8.1277 (3.8); 8.0899 (2.0); 8.0754 (3.3); 8.0358 (0.7); 7.9654(2.3); 7.9339 (0.8); 7.9196 (0.8); 7.7854 (1.0); 7.6280 (1.0); 7.4745(2.3); 7.3977 (0.9); 7.3482 (2.5); 6.3896 (0.4); 6.3782 (1.2); 6.3666(1.2); 6.3552 (0.4); 6.1410 (0.6); 6.1297 (0.6); 4.0663 (2.5); 4.0544(7.5); 4.0425 (7.5); 4.0306 (2.5); 3.6838 (0.4); 3.6732 (0.4); 3.5831(0.4); 3.5718 (0.4); 3.0814 (11.2); 3.0510 (4.5); 2.8869 (1.6); 2.8805(1.7); 2.8755 (1.9); 2.8714 (1.7); 2.2962 (34.3); 2.0964 (3.0); 2.0749(0.5); 2.0709 (0.7); 2.0668 (0.5); 1.9831 (41.8); 1.9761 (7.4); 1.9680(48.6); 1.9640 (84.1); 1.9599 (122.9); 1.9559 (86.2); 1.9518 (44.6);1.8526 (0.3); 1.8490 (0.5); 1.8448 (0.7); 1.8408 (0.6); 1.8367 (0.3);1.8223 (4.9); 1.8107 (5.0); 1.7571 (2.1); 1.7456 (2.1); 1.2162 (8.1);1.2043 (16.0); 1.1924 (8.0); 1.0754 (0.3); 0.5577 (0.5); 0.5476 (0.6);0.5368 (0.5); 0.4989 (0.4); 0.4923 (0.4); 0.4856 (0.5); 485.2 0.4790(0.5); 0.4725 (0.4); 0.4653 (0.4); 0.3417 (0.4); 0.3340 (0.4); 0.3278(0.3); 0.2872 (0.4); 0.2791 (0.6); 0.2723 (0.9); 0.2647 (1.1); 0.2572(0.9); 0.2499 (0.6); 0.2414 (0.4); 0.2386 (0.4); 0.2302 (0.6); 0.2229(0.6); 0.2163 (0.7); 0.2087 (0.5); −0.0016 (0.4); −0.1811 (0.6); −0.1892(0.8); −0.1972 (0.9) I-157

¹H-NMR (600.1 MHz, CD3CN, 260K): δ = 9.0327 (16.0); 8.4548 (5.9); 8.4540(6.0); 8.4510 (6.2); 8.4501 (5.8); 7.8325 (4.7); 7.8297 (7.4); 7.8267(4.9); 7.8011 (3.0); 7.7972 (3.0); 7.7860 (3.2); 7.7822 (3.1); 7.6933(4.7); 7.6908 (8.6); 7.6883 (4.7); 7.4471 (4.7); 7.4441 (8.3); 7.4411(4.6); 6.7266 (0.9); 2.9490 (0.6); 2.8797 (7.0); 2.2990 (65.2); 2.2665(0.5); 2.0807 (0.3); 2.0766 (0.6); 2.0725 (0.8); 2.0684 (0.6); 1.9986(0.9); 1.9903 (2.1); 1.9859 (31.8); 1.9778 (10.1); 1.9737 (10.2); 1.9699(57.1); 1.9658 (98.9); 1.9617 (145.3); 1.9575 (99.3); 1.9534 (50.6);1.9489 (1.3); 1.9447 (0.5); 1.8507 (0.6); 1.8466 (0.8); 1.8425 (0.6);1.6434 (0.4); 1.6280 (9.5); 1.6163 (9.4); 1.0757 (1.3); 1.0732 (1.2);1.0680 (5.3); 1.0648 (5.5); 1.0596 (2.4); 1.0571 (2.1); 1.0541 (5.4);1.0508 (5.3); 1.0458 (1.4); 1.0434 (1.5); 0.7685 (0.5); 0.7646 (0.4);0.7567 407.2 (2.8); 0.7516 (3.0); 0.7487 (6.1); 0.7450 (5.2); 0.7408(6.1); 0.7375 (3.2); 0.7326 (2.3); 0.7207 (0.3) I-158

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 10.6833 (7.3); 9.4272 (3.4); 9.4094(3.5); 8.9091 (6.3); 8.9035 (6.1); 8.4466 (3.9); 8.4400 (3.7); 8.4244(4.3); 8.4179 (4.2); 8.3162 (1.0); 8.2696 (4.8); 8.2659 (9.1); 8.2621(5.4); 8.1553 (4.4); 8.1506 (7.7); 8.1467 (5.8); 8.1392 (16.0); 8.1237(5.7); 8.1194 (7.9); 8.1149 (4.1); 8.0932 (5.0); 8.0879 (2.2); 8.0795(5.6); 8.0710 (6.0); 8.0627 (2.2); 8.0573 (5.4); 8.0497 (0.6); 7.9524(1.2); 7.8574 (6.3); 7.8352 (6.0); 7.4402 (5.5); 7.4350 (1.8); 7.4180(10.6); 7.4010 (1.7); 7.3958 (5.3); 7.2766 (0.3); 7.2541 (0.6); 6.0225(0.5); 6.0052 (2.3); 5.9877 (3.6); 5.9702 (2.3); 5.9526 (0.5); 3.3262(194.2); 3.3081 (39.6); 3.2623 (0.5); 3.1453 (0.4); 2.8911 (8.4); 2.7321(7.0); 2.7311 (7.2); 2.6759 (1.7); 2.6713 (2.3); 2.6667 (1.7); 2.6621(0.8); 2.5248 (7.2); 2.5200 (10.8); 2.5113 (141.6); 2.5069 (287.7);2.5023 (375.5); 2.4977 (268.6); 2.4933 (128.8); 2.3383 (0.8); 2.3337(1.6); 2.3292 (2.3); 2.3246 (1.6); 2.3202 (0.8); 2.0749 (1.0); 1.6548(13.2); 1.6374 (13.1); 0.1459 (0.8); 0.0079 (6.8); −0.0002 (207.1);−0.0085 (6.8); −0.1495 (0.8) 543.1 I-159

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.1139 (1.2); 9.0960 (1.2); 9.0284(2.2); 9.0267 (2.3); 9.0230 (2.4); 9.0212 (2.1); 8.5414 (1.9); 8.5358(1.8); 8.5199 (2.0); 8.5143 (2.0); 8.0164 (2.4); 8.0147 (2.3); 7.9949(2.2); 7.9931 (2.1); 7.6057 (1.7); 7.6014 (2.7); 7.5970 (1.8); 7.4270(1.6); 7.4234 (2.8); 7.4198 (1.6); 7.3291 (1.6); 7.3248 (2.7); 7.3204(1.5); 6.0602 (1.0); 6.0428 (1.5); 6.0251 (1.0); 4.0380 (0.6); 4.0202(0.5); 3.3262 (51.1); 2.6760 (0.4); 2.6715 (0.5); 2.6669 (0.4); 2.5251(1.4); 2.5204 (2.0); 2.5116 (28.6); 2.5072 (59.3); 2.5026 (78.4); 2.4980(55.5); 2.4935 (25.8); 2.3374 (16.0); 2.3250 (0.5); 2.0029 (0.6); 1.9944(0.6); 1.9892 (2.8); 1.9820 (1.2); 1.9694 (0.6); 1.9612 (0.6); 1.6044(5.5); 1.5870 (5.4); 1.2342 (0.4); 1.1931 (0.7); 1.1753 (1.4); 1.1575(0.7); 1.0181 (0.6); 1.0072 (1.9); 1.0016 (2.0); 0.9975 (0.9); 0.9914(0.9); 0.9862 (2.0); 0.9807 (2.0); 0.9706 (0.7); 0.7720 (0.9); 407.30.7616 (2.0); 0.7593 (1.7); 0.7561 (1.9); 0.7492 (2.0); 0.7444 (2.0);0.7330 (0.7); −0.0002 (6.7) I-160

¹H-NMR (600.4 MHz, d₆-DMSO): δ = 9.1666 (0.4); 9.1550 (0.4); 9.0552(0.7); 9.0544 (0.7); 9.0517 (0.7); 9.0508 (0.7); 8.5739 (0.6); 8.5702(0.5); 8.5596 (0.6); 8.5559 (0.6); 8.2349 (1.7); 8.0696 (0.7); 8.0688(0.7); 8.0554 (0.7); 8.0545 (0.7); 7.7163 (0.6); 7.7137 (1.0); 7.7111(0.6); 7.6725 (0.6); 7.6696 (0.9); 7.6669 (0.6); 7.5624 (0.6); 7.5594(1.0); 7.5564 (0.5); 6.0511 (0.5); 4.0357 (0.4); 4.0238 (0.4); 3.3091(35.4); 2.5218 (0.4); 2.5188 (0.4); 2.5157 (0.4); 2.5068 (10.8); 2.5038(22.6); 2.5008 (31.0); 2.4978 (22.9); 2.4949 (10.9); 1.9880 (1.9);1.6390 (1.9); 1.6274 (1.9); 1.3980 (0.3); 1.2794 (16.0); 1.1868 (0.5);1.1749 (1.0); 1.1631 (0.5); −0.0001 (1.8) 409.2 I-161

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.6492 (3.3); 9.6318 (3.4); 9.0777(5.9); 9.0758 (6.4); 9.0722 (6.4); 9.0702 (6.1); 8.6235 (6.5); 8.5881(5.7); 8.5826 (5.4); 8.5667 (6.0); 8.5611 (6.0); 8.4814 (5.7); 8.3981(5.6); 8.3967 (5.6); 8.3128 (1.7); 8.2604 (16.0); 8.0942 (6.8); 8.0923(6.7); 8.0727 (6.2); 8.0708 (6.4); 6.1740 (0.5); 6.1569 (2.4); 6.1396(3.8); 6.1222 (2.4); 6.1048 (0.5); 3.3751 (41.7); 3.3144 (246.9); 2.6795(1.2); 2.6749 (2.6); 2.6703 (3.6); 2.6657 (2.6); 2.6612 (1.2); 2.5239(10.4); 2.5192 (15.1); 2.5105 (192.1); 2.5059 (393.4); 2.5013 (530.3);2.4967 (389.4); 2.4921 (187.4); 2.3375 (1.1); 2.3328 (2.4); 2.3282(3.4); 2.3236 (2.4); 2.3190 (1.1); 2.0729 (1.2); 1.6743 (14.2); 1.6569(14.2); 0.1460 (1.6); 0.0081 (13.7); −0.0002 (445.3); −0.0085 (13.4);−0.0194 (0.5); 465.2 −0.1495 (1.6) I-162

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.0102 (5.6); 9.0084 (6.2); 9.0047(6.6); 9.0028 (6.6); 8.9869 (2.8); 8.9726 (1.4); 8.5050 (4.7); 8.4994(4.5); 8.4855 (5.1); 8.4779 (5.0); 8.3158 (1.2); 8.2394 (4.5); 8.2356(8.4); 8.2318 (5.2); 8.2250 (16.0); 8.1458 (4.3); 8.1412 (7.7); 8.1369(5.0); 8.1092 (5.2); 8.1052 (6.8); 8.1006 (3.9); 8.0392 (5.8); 8.0375(5.8); 8.0177 (5.3); 8.0159 (5.4); 3.7736 (1.4); 3.7569 (4.1); 3.7418(4.6); 3.7260 (2.0); 3.5949 (3.9); 3.5785 (6.9); 3.5611 (2.6); 3.3274(509.9); 2.6802 (0.9); 2.6758 (2.0); 2.6712 (2.8); 2.6667 (2.0); 2.6622(0.9); 2.5247 (8.9); 2.5199 (13.4); 2.5113 (168.8); 2.5068 (343.5);2.5023 (450.2); 2.4977 (321.6); 2.4932 (153.1); 2.3380 (0.9); 2.3336(2.0); 2.3291 (2.8); 2.3246 (2.0); 0.1459 (1.3); 0.0080 (10.8); −0.0001(323.8); −0.0085 (11.0); −0.1496 (1.3) 431.1 I-163

¹H-NMR (600.4 MHz, d₆-DMSO): δ = 10.6902 (5.8); 9.4349 (3.3); 9.4233(3.5); 8.7287 (5.4); 8.7244 (5.5); 8.2874 (3.0); 8.2831 (2.9); 8.2727(3.2); 8.2684 (3.3); 8.2155 (3.6); 8.2131 (7.2); 8.2108 (4.8); 8.1287(3.3); 8.1256 (6.3); 8.1229 (4.1); 8.0836 (4.0); 8.0807 (6.3); 8.0782(4.0); 7.8063 (5.5); 7.7917 (5.3); 5.9021 (0.5); 5.8907 (2.2); 5.8791(3.5); 5.8675 (2.3); 5.8558 (0.5); 3.3103 (82.9); 3.3040 (33.9); 2.6168(0.4); 2.6138 (0.6); 2.6108 (0.5); 2.5227 (1.0); 2.5198 (1.4); 2.5167(1.4); 2.5047 (71.2); 2.5018 (100.3); 2.4988 (77.1); 2.3887 (0.4);2.3857 (0.6); 2.3827 (0.4); 2.0861 (16.0); 1.8250 (0.6); 1.8139 (1.5);1.8095 (0.9); 1.8045 (2.4); 1.8002 (1.0); 1.7953 (1.4); 1.7931 (1.4);1.7839 (0.7); 1.6683 (11.9); 1.6567 (12.0); 0.8893 (0.4); 0.8787 (1.8);0.8740 (6.7); 0.8680 (7.6); 0.8607 (15.1); −0.0001 (0.7) 557.1 I-164

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4131 (1.3); 9.3952 (1.3); 8.3156(0.5); 8.2772 (2.0); 8.2735 (3.5); 8.2697 (2.1); 8.2454 (1.9); 8.2393(1.8); 8.1606 (1.9); 8.1560 (3.0); 8.1520 (2.2); 8.1276 (2.4); 8.1232(3.3); 8.1187 (1.8); 8.1117 (5.8); 7.8251 (0.8); 7.8185 (0.8); 7.8031(1.5); 7.7966 (1.5); 7.7594 (2.1); 7.7376 (1.0); 5.9608 (0.9); 5.9433(1.3); 5.9258 (0.8); 4.0556 (1.5); 4.0378 (4.0); 4.0200 (4.0); 4.0023(1.6); 3.8546 (0.7); 3.8511 (0.8); 3.8018 (0.8); 3.7985 (0.8); 3.7725(0.8); 3.6694 (0.7); 3.6657 (0.7); 3.6463 (0.7); 3.5931 (0.5); 3.5087(0.4); 3.4824 (0.4); 3.3921 (1.0); 3.3701 (0.6); 3.3564 (0.4); 3.3425(0.4); 3.3346 (0.5); 3.3290 (0.8); 3.3110 (15.6); 3.2771 (0.5); 3.2664(0.3); 3.2594 (0.5); 3.2487 (0.3); 3.2436 (0.4); 3.2261 (0.4); 3.1165(0.5); 3.1046 (0.5); 3.0983 (0.5); 3.0863 (0.5); 2.7774 (4.7); 2.7390(8.6); 2.6897 (0.4); 2.6735 (9.1); 2.6351 (4.6); 2.6243 (0.6); 2.5249(4.0); 2.5200 (6.3); 2.5114 (68.3); 2.5070 (136.0); 2.5025 553.1(176.1); 2.4979 (125.0); 2.4934 (59.0); 2.3384 (0.4); 2.3339 (0.8);2.3293 (1.0); 2.3248 (0.8); 2.3203 (0.4); 2.2914 (0.6); 1.9889 (16.0);1.9799 (0.3); 1.9620 (1.4); 1.9089 (0.6); 1.6249 (5.2); 1.6076 (5.2);1.2443 (0.5); 1.2352 (0.7); 1.1929 (5.1); 1.1751 (10.3); 1.1573 (5.1);1.1096 (0.5); 1.0918 (0.9); 1.0740 (0.4); 1.0127 (0.6); 0.9950 (0.7);0.1459 (0.5); 0.0079 (4.6); −0.0002 (129.1); −0.0085 (4.6); −0.1496(0.6) I-165

¹H-NMR (600.1 MHz, CD3CN, 260K): δ = 8.8223 (0.8); 8.8190 (0.8); 8.3722(0.5); 8.3687 (0.5); 8.3579 (0.5); 8.3542 (0.5); 8.2881 (0.8); 8.2714(0.5); 8.2678 (0.4); 8.1192 (1.7); 8.0806 (1.8); 8.0648 (0.8); 7.8997(0.6); 7.8856 (0.6); 7.1249 (0.9); 6.9138 (0.9); 6.8939 (0.8); 6.7695(0.4); 6.6870 (1.0); 6.5936 (0.4); 6.4763 (0.5); 6.4648 (0.5); 6.1780(0.4); 6.1664 (0.4); 2.2903 (29.8); 2.0800 (0.4); 2.0761 (0.7); 2.0720(0.8); 2.0677 (0.7); 2.0634 (0.7); 1.9854 (4.6); 1.9773 (3.7); 1.9730(5.1); 1.9694 (49.8); 1.9653 (92.5); 1.9612 (136.4); 1.9571 (94.9);1.9530 (49.1); 1.9446 (1.4); 1.9357 (0.6); 1.9320 (0.4); 1.9008 (0.4);1.8944 (0.3); 1.8866 (0.5); 1.8542 (0.3); 1.8502 (0.6); 1.8461 (0.8);1.8420 (0.6); 1.8379 (0.3); 1.7415 (1.8); 1.7351 (0.5); 1.7299 (1.8);1.7066 (2.0); 1.6949 (2.0); 1.0131 (0.6); 1.0033 (0.9); 0.9997 (1.3);0.9896 (0.8); 0.9861 (0.7); 0.6605 (0.8); 0.6576 (0.8); 0.6523 (0.8);0.6493 (0.8); 0.5643 (0.5); 0.5574 (0.4); 0.0968 (1.1); 0.0690 (13.2);0.0053 (7.1); −0.0001 (226.7); −0.0055 (8.8); −0.0197 (0.6); −0.0233(0.4); −0.0259 (0.6); −0.0290 (0.3); −0.1001 (1.2); −0.3567 (16.0) 493.2I-166

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4742 (2.9); 9.4568 (2.9); 9.1700(6.8); 9.1671 (7.0); 8.7639 (6.3); 8.7575 (7.2); 8.6712 (4.6); 8.6677(5.1); 8.6649 (4.7); 8.6613 (4.2); 8.3142 (0.8); 8.2630 (16.0); 8.2564(4.9); 8.1629 (3.4); 8.1583 (6.7); 8.1544 (4.9); 8.1389 (4.8); 8.1346(6.7); 8.1300 (3.3); 6.0031 (0.5); 5.9858 (2.2); 5.9685 (3.4); 5.9511(2.2); 5.9337 (0.5); 3.3232 (241.0); 3.3152 (43.0); 2.6755 (1.3); 2.6709(1.8); 2.6665 (1.3); 2.6615 (0.7); 2.5244 (5.4); 2.5196 (8.2); 2.5109(100.6); 2.5065 (203.5); 2.5019 (273.3); 2.4974 (205.3); 2.4930 (102.7);2.3379 (0.6); 2.3333 (1.2); 2.3288 (1.8); 2.3243 (1.3); 2.0738 (0.4);1.6576 (13.0); 407.1 1.6402 (13.0); 0.1459 (0.8); 0.0080 (6.0); −0.0002(184.4); −0.0085 (6.6); −0.1496 (0.8) I-167

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 11.9576 (0.3); 9.7724 (0.4); 9.4649(3.4); 9.4473 (3.5); 8.8634 (4.9); 8.8505 (5.0); 8.3211 (0.5); 8.3082(0.5); 8.2730 (4.8); 8.2691 (9.5); 8.2653 (5.7); 8.2438 (16.0); 8.1547(3.0); 8.1498 (8.7); 8.1458 (8.2); 8.1440 (9.3); 8.1397 (8.6); 8.1349(3.4); 8.1271 (6.8); 8.1255 (6.4); 7.9030 (3.5); 7.9007 (3.5); 7.8901(3.4); 7.8878 (3.3); 7.2261 (0.6); 6.9739 (0.3); 6.1130 (0.5); 6.0958(2.5); 6.0783 (3.9); 6.0608 (2.5); 6.0435 (0.5); 4.0392 (0.8); 4.0214(0.8); 3.3458 (0.9); 3.3236 (35.6); 3.3163 (41.6); 2.6775 (0.4); 2.6728(0.6); 2.6681 (0.4); 2.5264 (1.8); 2.5217 (2.6); 2.5129 (31.4); 2.5084(64.5); 2.5038 (87.6); 2.4992 (65.6); 2.4947 (32.2); 2.3352 (0.4);2.3307 (0.5); 2.3262 (0.4); 2.0874 (1.3); 1.9898 (3.4); 1.9795 (4.3);1.9421 (4.5); 474.2 1.9103 (11.7); 1.6624 (14.6); 1.6450 (14.7); 1.1940(0.9); 1.1762 (1.8); 1.1584 (0.9); 0.0081 (2.3); −0.0002 (72.7); −0.0085(2.3) I-168

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.4437 (2.8); 9.4259 (2.8); 8.5768(2.7); 8.5750 (2.7); 8.5724 (2.9); 8.5647 (2.8); 8.5629 (2.8); 8.5602(2.7); 8.3146 (0.5); 8.2681 (4.3); 8.2644 (7.2); 8.2606 (3.9); 8.1603(4.2); 8.1560 (7.3); 8.1514 (16.0); 8.1342 (4.9); 8.1301 (6.5); 8.1254(2.8); 8.1060 (1.7); 8.1013 (1.6); 8.0869 (3.0); 8.0823 (2.8); 8.0668(2.2); 8.0621 (2.0); 7.8687 (4.7); 7.8483 (3.9); 7.5103 (2.4); 7.5081(2.1); 7.4981 (2.4); 7.4959 (2.4); 7.4917 (2.4); 7.4795 (2.2); 7.4773(1.9); 6.0849 (0.5); 6.0677 (2.0); 6.0501 (3.2); 6.0326 (2.0); 6.0154(0.4); 3.3226 (111.6); 2.6756 (1.1); 2.6711 (1.4); 2.6667 (1.0); 2.6624(0.5); 2.5243 (6.0); 2.5110 406.2 (93.9); 2.5066 (173.2); 2.5021(219.2); 2.4976 (157.4); 2.4933 (74.8): 2.3379 (0.5); 2.3334 (1.1);2.3289 (1.4); 2.3245 (1.0); 2.3201 (0.4); 2.0740 (0.4); 1.9466 (0.6);1.9001 (0.6); 1.6483 (12.3); 1.6309 (12.1); 0.1462 (0.6); 0.0079 (7.1);−0.0002 (141.2); −0.0085 (4.5); −0.0137 (0.4); −0.1492 (0.6) I-169

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.2218 (2.5); 9.2039 (2.6); 8.5670(2.6); 8.5643 (2.7); 8.5625 (2.5); 8.5566 (2.4); 8.5548 (2.8); 8.5522(2.7); 8.5503 (2.4); 8.3162 (0.4); 8.1400 (12.2); 8.1041 (1.7); 8.0994(1.7); 8.0837 (2.7); 8.0805 (2.6); 8.0791 (2.7); 8.0649 (2.2); 8.0602(2.2); 7.8599 (4.8); 7.8394 (4.1); 7.7703 (3.7); 7.7661 (6.0); 7.7620(4.2); 7.6602 (3.8); 7.6561 (6.4); 7.6523 (4.0); 7.5130 (4.0); 7.5082(8.3); 7.5043 (5.3); 7.4951 (2.2); 7.4928 (2.4); 7.4887 (2.3); 7.4863(2.2); 7.4764 (2.1); 7.4741 (2.1); 6.0421 (0.4); 6.0249 (2.0); 6.0073(3.1); 5.9898 (2.0); 5.9722 (0.4); 4.0557 (1.2); 4.0379 (3.6); 4.0201(3.6); 4.0023 (1.2); 3.3291 393.3 (235.5); 2.6759 (0.9); 2.6715 (1.2);2.6670 (0.9); 2.5249 (3.9); 2.5202 (5.7); 2.5115 (74.0); 2.5071 (152.1);2.5025 (200.7); 2.4980 (145.3); 2.4935 (70.4); 2.3385 (0.4); 2.3339(0.9); 2.3294 (1.2); 2.3249 (0.9); 2.3202 (0.4); 1.9891 (16.0); 1.8114(2.1); 1.7991 (6.1); 1.7916 (6.6); 1.7803 (2.8); 1.7407 (0.4); 1.6623(0.5); 1.6356 (12.2); 1.6182 (12.9); 1.6114 (7.6); 1.6038 (6.5); 1.5908(2.3); 1.3975 (2.9); 1.2493 (0.4); 1.2369 (0.5); 1.1929 (4.3); 1.1751(8.6); 1.1573 (4.2); 0.1458 (0.6); 0.0079 (4.6); −0.0002 (146.1);−0.0086 (5.1); −0.1497 (0.6) I-170

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.2142 (2.5); 9.1965 (2.6); 8.6280(4.7); 8.6226 (4.7); 8.6216 (4.6); 8.2105 (3.6); 8.2040 (3.4); 8.1887(4.0); 8.1822 (4.0); 8.1662 (11.5); 7.8852 (5.2); 7.8842 (5.2); 7.8633(4.5); 7.8623 (4.6); 7.7690 (3.4); 7.7648 (5.5); 7.7606 (3.9); 7.6678(3.5); 7.6638 (6.0); 7.6599 (3.6); 7.5193 (3.6); 7.5147 (6.4); 7.5101(3.3); 5.9902 (0.4); 5.9729 (1.8); 5.9554 (2.8); 5.9379 (1.8); 5.9205(0.4); 5.7527 (8.4); 3.3186 (5.7); 2.5264 (0.8); 2.5217 (1.2); 2.5130(13.9); 2.5085 (28.3); 2.5039 (38.6); 2.4993 (28.9); 2.4948 (14.3);1.9897 (0.4); 1.8142 (1.9); 1.8018 (5.6); 1.7943 (6.0); 1.7828 (2.6);1.7434 (0.4); 1.6649 (0.4); 1.6313 (10.7); 1.6269 (4.8); 1.6139 (16.0);1.6067 (6.6); 1.5934 (2.1); 0.0080 (1.1); −0.0002 (33.5); −0.0085 (1.1)427.2 I-171

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.2443 (3.6); 9.2268 (3.6); 9.1602(8.5); 9.1569 (8.7); 8.7587 (8.0); 8.7524 (9.0); 8.6618 (5.9); 8.6582(6.4); 8.6555 (6.1); 8.6518 (5.3); 8.2521 (15.6); 7.7652 (4.9); 7.7609(8.1); 7.7569 (5.6); 7.6541 (5.1); 7.6501 (8.7); 7.6463 (5.3); 7.5178(5.2); 7.5132 (9.2); 7.5087 (4.8); 5.9645 (0.6); 5.9471 (2.6); 5.9298(4.2); 5.9123 (2.7); 5.8948 (0.6); 5.7552 (0.3); 3.3236 (59.4); 2.6766(0.4); 2.6721 (0.6); 2.6677 (0.4); 2.5257 (1.7); 2.5211 (2.5); 2.5122(33.3); 2.5078 (68.1); 2.5032 (93.4); 2.4987 (71.3); 2.4942 (35.8);2.3347 (0.4); 2.3301 (0.6); 2.3256 (0.4); 1.8109 (2.8); 1.7988 (7.7);1.7912 (8.5); 1.7799 (3.6); 394.3 1.7399 (0.5); 1.6614 (0.8); 1.6461(15.7); 1.6287 (16.0); 1.6226 (5.9); 1.6103 (8.6); 1.6027 (7.9); 1.5901(3.2); 1.2501 (0.4); 1.2357 (0.6); 0.0081 (2.2); −0.0002 (71.2); −0.0085(2.6) I-172

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.2548 (3.4); 9.2372 (3.5); 8.9804(4.3); 8.9785 (4.2); 8.9766 (4.3); 8.9744 (4.5); 8.4988 (2.6); 8.4928(2.6); 8.4771 (2.9); 8.4711 (2.8); 8.2338 (16.0); 8.0946 (4.8); 8.0731(4.4); 7.7734 (4.5); 7.7691 (7.2); 7.7651 (5.3); 7.6780 (4.6); 7.6738(8.0); 7.6700 (5.0); 7.5165 (4.8); 7.5119 (8.8); 7.5073 (4.6); 6.1056(0.5); 6.0883 (2.3); 6.0708 (3.6); 6.0534 (2.3); 6.0359 (0.5); 3.3246(36.7); 2.6735 (0.4); 2.5271 (1.2); 2.5224 (1.8); 2.5137 (21.9); 2.5091(45.2); 2.5045 (62.4); 2.4999 (47.2); 2.4954 (23.1); 2.3314 (0.4);1.8120 (2.6); 1.8000 (7.0); 1.7924 (7.7); 1.7811 (3.3); 1.7411 (0.4);1.6556 (13.6); 1.6382 (13.6); 1.6211 (4.0); 1.6090 (7.7); 1.6013 (7.0);1.5887 (2.8); 0.0081 (1.7); −0.0002 (53.2); −0.0085 (1.6) 461.3 I-173

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.3612 (6.9); 9.3555 (6.9); 9.3544(6.7); 9.3018 (3.5); 9.2845 (3.6); 8.8517 (5.3); 8.8448 (5.1); 8.8291(5.6); 8.8222 (5.6); 8.3141 (0.4); 8.2703 (16.0); 8.1540 (7.2); 8.1531(7.4); 8.1316 (6.8); 8.1305 (7.0); 7.8185 (4.8); 7.8144 (7.8); 7.8102(5.5); 7.7144 (5.0); 7.7103 (8.5); 7.7064 (5.2); 7.5215 (5.1); 7.5168(9.3); 7.5122 (4.9); 6.1390 (0.5); 6.1218 (2.6); 6.1045 (4.0); 6.0871(2.6); 6.0696 (0.5); 4.0384 (0.7); 4.0206 (0.7); 3.3244 (166.1); 2.6763(0.6); 2.6717 (0.9); 2.6671 (0.6); 2.5252 (2.6); 2.5205 (3.8); 2.5118(47.6); 2.5073 (98.1); 2.5027 (133.4); 2.4981 (100.3); 2.4936 (49.7);2.3341 (0.6); 2.3296 (0.8); 2.3250 (0.6); 1.9891 (3.3); 1.8127 (2.7);1.8004 (7.8); 1.7928 (8.4); 1.7815 (3.6); 1.7419 (0.5); 1.6595 (15.2);1.6421 438.2 (15.2); 1.6311 (4.5); 1.6187 (8.3); 1.6113 (7.9); 1.5982(2.9); 1.1933 (0.9); 1.1755 (1.8); 1.1577 (0.9); 0.1459 (0.4); 0.0080(3.1); −0.0002 (98.8); −0.0085 (3.2); −0.1497 (0.4) I-174

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.2250 (2.5); 9.2070 (2.6); 8.9923(15.6); 8.9801 (16.0); 8.1610 (12.0); 7.9154 (0.4); 7.8109 (0.5); 7.7434(3.7); 7.7392 (5.9); 7.7351 (4.2); 7.6433 (4.0); 7.6392 (10.6); 7.6355(4.3); 7.6269 (8.2); 7.6147 (4.2); 7.5546 (0.5); 7.5126 (4.0); 7.5080(7.0); 7.5034 (3.7); 6.0090 (0.4); 5.9915 (2.0); 5.9739 (3.0); 5.9562(2.0); 5.9387 (0.4); 3.3187 (8.9); 2.6762 (0.4); 2.6716 (0.5); 2.6670(0.4); 2.5419 (0.5); 2.5251 (1.6); 2.5203 (2.3); 2.5117 (30.8); 2.5072(62.9); 2.5026 (83.6); 2.4980 (61.4); 2.4935 (30.1); 2.3341 (0.4);2.3294 (0.5); 2.3249 (0.4); 1.8255 (0.5); 1.8179 (0.6); 1.8084 (2.3);1.7971 (5.5); 1.7893 (6.3); 394.2 1.7782 (2.9); 1.7374 (0.3); 1.6589(0.6); 1.6415 (12.2); 1.6241 (12.2); 1.6196 (5.4); 1.6109 (3.7); 1.6075(6.3); 1.6018 (4.3); 1.5993 (5.1); 1.5879 (2.5); 1.4177 (0.9); 1.3996(0.9); 0.0080 (1.6); −0.0002 (50.7); −0.0085 (1.8) I-175

¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.6625 (3.5); 9.6453 (3.6); 9.0583(5.8); 9.0566 (6.4); 9.0528 (6.5); 9.0511 (6.2); 8.5839 (5.0); 8.5784(4.9); 8.5625 (5.3); 8.5569 (5.4); 8.3896 (7.3); 8.3222 (6.5); 8.3037(7.9); 8.3003 (7.6); 8.2622 (16.0); 8.0904 (6.5); 8.0888 (6.6); 8.0689(5.9); 8.0673 (6.1); 6.1507 (0.6); 6.1334 (2.5); 6.1161 (4.0); 6.0988(2.5); 6.0815 (0.5); 5.7545 (3.7); 3.3546 (0.7); 3.3267 (267.7); 2.6814(0.4); 2.6769 (0.7); 2.6725 (1.0); 2.6678 (0.7); 2.6635 (0.4); 2.5258(3.2); 2.5211 (4.7); 2.5124 (55.1); 2.5080 (111.5): 2.5034 (148.3);2.4988 (110.5); 2.4944 (55.3); 2.3348 (0.6); 2.3302 (0.9); 2.3256 (0.7);1.6664 (15.0); 1.6490 (15.0); 1.2343 (0.9); 0.1459 (0.3); 0.0080 (2.4);−0.0002 (75.5); −0.0084 (2.9); −0.1497 (0.3) 469.2 ¹⁾‘260K’ denotes thatthe measurement was conducted at 260K. ²⁾The stated mass corresponds tothe peak from the isotope pattern of the [M − H]⁻ ion with the highestintensity. ^(#)denotes that the [M − H]⁻ ion was recorded.

TABLE 2 (Intermediates) ESI mass Example Structure NMR¹⁾ [m/z]²⁾ a*-001

¹H NMR (400 MHz, d₆-DMSO): δ = 9.13-9.11 (d, 1H, NH), 8.61 (s, 1H), 8.54(s, 1H), 8.41 (s, 1H), 7.50 (br s, 1H from NH₂), 7.05 (br s, 1H fromNH₂), 4.46-4.39 (m, 1H), 1.36-1.35 (d, 3H). 358.9  a*-002

¹H NMR (400 MHz, d₆-DMSO): δ = 8.92 (d, 1H), 8.37 (t, 1H), 8.30 (t, 1H),8.14 (t, 1H), 7.47 (br s, 1H), 7.04 (br s, 1H), 4.46-4.39 (m, 1H), 3.34(s, 3H), 1.35 (d, 3H). 305.1  a*-003

¹H NMR (400 MHz, d₆-DMSO): δ = 8.72 (d, 1H), 7.90 (t, 1H), 7.79 (t, 1H),7.53 (t, 1H), 7.42 (br s, 1H), 7.01 (br s, 1H), 4.42-4.38 (m, 1H), 1.83-1.80 (m, 2H), 1.66-1.63 (m, 2H), 1.34 (d, 3H). 292.2  b*-001

¹H NMR (400 MHz, CDCl₃): δ = 11.28 (br s, 1H), 8.29 (s, 1H), 8.20-8.25(m, 1H), 7.91 (s, 1H).³⁾ 254.8^(#) b*-002

¹H NMR (400 MHz, CDCl₃): δ = 8.20 (s, 1H), 8.10- 8.15 (m, 1H), 7.83 (s,1H), 3.96 (s, 3H).³⁾ b*-003

¹H NMR (400 MHz, d₆-DMSO): δ = 14.27-14.20 (br s, 1H), 8.51 (s, 1H),8.49 (s, 1H), 8.38 (s, 1H). 287.0^(#) b*-004

¹H NMR (400 MHz, d₆-DMSO): δ = 13.76 (br s, 1H), 8.03 (s, 1H), 7.98-7.95(m, 1H), 7.93-7.89 (m, 1H). 239.1^(#) c*-001

¹H NMR (400 MHz, Varian machine, MeOD): δ = 7.89 (s, 1H), 7.88 (s, 1H),7.54 (s, 1 H), 1.78-1.82 (m, 2 H), 1.55-1.59 (m, 2 H). 220.1^(#) d*-001

¹H NMR (400 MHz, d₆-DMSO): δ = 13.92 (br s, 1H), 8.27 (t, J = 1.6 Hz,1H), 8.25-8.20 (m, 2H), 3.13-3.05 (m, 1H), 1.25-1.05 (m, 4 H). 259.1^(#)d*-002

¹H NMR (400 MHz, d₆-DMSO): δ = 13.90 (br s, 1H), 8.27 (t, J = 1.4 Hz,1H), 8.23 (t, J = 1.0 Hz, 1H), 8.21 (t, J = 1.8 Hz, 1H), 3.46 (q, J =7.2 Hz 2H), 1.12 (t, J = 7.2 Hz 3H). 247.1^(#) d*-003

¹H NMR (400 MHz, d₆-DMSO): δ = 13.94 (br s, 1H), 8.34 (t, J = 1.4 Hz,1H), 8.32-8.30 (m, 1H), 8.22-8.14 (m, 3H), 7.53-7.45 (m, 2H). 313.0^(#)d*-004

¹H NMR (400 MHz, d₆-DMSO): δ = 13.55 (br s, 1H), 7.97-7.92 (m, 2H), 7.79(t, J = 1.8 Hz, 1H), 1.27 (s, 9H). 243.1^(#) d*-005

¹H NMR (400 MHz, d₆-DMSO): δ = 13.50 (br s, 1H), 7.77 (t, J = 1.6 Hz,1H), 7.72 (t, J = 1.8 Hz, 1H), 7.67 (t, J = 1.8 Hz, 1H), 3.67 (sep, J =6.8 Hz 1H), 1.27 (d, J = 6.8 Hz 6H). 229.1^(#) d*-006

¹H NMR (400 MHz, d₆-DMSO): δ = 13.55 (br s, 1H), 7.94-7.88 (m, 2H), 7.77(t, J = 1.6 Hz, 1H), 4.20 (q, J = 10.3 Hz 2H). 269.0^(#) e*-001

¹H NMR (400 MHz, d₆-DMSO): δ = 13.37 (br s, 1H), 7.65 (t, J = 1.6 Hz,1H), 7.58-7.54 (m, 1H), 7.34 (br s, 1H), 2.14-2.05 (m, 1H), 1.10-1.00(m, 2H), 0.85-0.75 (m, 2 H). 245.1^(#) ¹⁾‘260 K’ denotes that themeasurement was conducted at 260 K. ²⁾The stated mass corresponds to thepeak from the isotope pattern of the [M + H]⁺ ion with the highestintensity. ^(#)denotes that the [M − H]⁻ ion was recorded. ³⁾Referencedto the signal of trace CHCl₃ at 7.25 ppm.

Biological Examples

Ctenocephalides felis—In-Vitro Contact Test Adult Cat Flea

9 mg compound is solved in 1 ml acetone and diluted with acetone to thedesired concentration. 250 μl of the test solution is filled in 25 mlglass test tubes and homogeneously distributed on the inner walls byrotation and tilting on a shaking device (2 h at 30 rpm). With acompound concentration of 900 ppm, an inner surface of 44.7 cm² and ahomogeneous distribution, a dose of 5 μg/cm² is achieved.

After the solvent has evaporated, each test tube is filled with 5-10adult cat fleas (Ctenocephalides felis), closed with a perforated lidand incubated in a lying position at room temperature and relativehumidity. After 48 hours efficacy is determined. The fleas are patted onthe ground of the tubes and are incubated on a heating plate at 45-50°C. for at most 5 minutes. Immotile or uncoordinated moving fleas, whichare not able to escape the heat by climbing upwards, are marked as deador moribund.

A compound shows a good efficacy against Ctenocephalides felis, if at acompound concentration of 5 μg/cm² an efficacy of at least 80% ismonitored. An efficacy of 100% means all fleas are dead or moribund; 0%means no fleas are dead or moribund.

In this test, for example, the following compounds from the preparationexamples showed good activity of 100% at an application rate of 5 μg/cm²(=500 g/ha): I-002, I-003, I-007, I-019, I-020, I-021, I-024, I-025,I-034, I-035, I-036, I-037, I-038, I-039, I-040, I-042, I-044, I-045,I-046, I-050, I-057, I-066, I-069, I-070, I-089, I-091, I-095.

In this test, for example, the following compounds from the preparationexamples showed good activity of 90% at an application rate of 5 μg/cm²(=500 g/ha): I-005, I-006, I-041, I-043, I-067, I-068, I-073, I-074,I-075, I-098.

In this test, for example, the following compounds from the preparationexamples showed good activity of 80% at an application rate of 5 μg/cm²(=500 g/ha): I-001, I-051, I-054, I-059, I-092.

Rhipicephalus sanguineus—In-Vitro Contact Test with Adult Brown DogTicks

9 mg compound is solved in 1 ml acetone and diluted with acetone to thedesired concentration. 250 μl of the test solution is filled in 25 mlglass test tubes and homogeneously distributed on the inner walls byrotation and tilting on a shaking device (2 h at 30 rpm). With acompound concentration of 900 ppm, an inner surface of 44.7 cm² and ahomogeneous distribution, a dose of 5 μg/cm² is achieved.

After the solvent has evaporated, each test tube is filled with 5-10adult brown dog ticks (Rhipicephalus sanguineus), closed with aperforated lid and incubated in a lying position at room temperature andrelative humidity. After 48 hours efficacy is determined. The ticks arepatted on the ground of the tubes and are incubated on a heating plateat 45-50° C. for at most 5 minutes. Immotile or uncoordinated movingticks, which are not able to escape the heat by climbing upwards, aremarked as dead or moribund.

A compound shows a good efficacy against Rhipicephalus sanguineus, if ata compound concentration of 5 μg/cm² an efficacy of at least 80% ismonitored. An efficacy of 100% means all ticks are dead or moribund; 0%means no ticks are dead or moribund.

In this test, for example, the following compounds from the preparationexamples showed good activity of 100% at an application rate of 5 μg/cm²(=500 g/ha): I-001, I-003, I-040, I-045, I-053.

In this test, for example, the following compounds from the preparationexamples showed good activity of 80% at an application rate of 5 μg/cm²(=500 g/ha): I-002, I-004, I-006, I-021, I-034, I-036, I-037, I-042,I-066.

Boophilus microplus—Injection Test

Solvent: dimethyl sulfoxide

To produce a suitable preparation of active compound, 10 mg of activecompound are dissolved in 0.5 ml solvent, and the concentrate is dilutedwith solvent to the desired concentration.

Five adult engorged female ticks (Boophilus microplus) are injected with1 μl compound solution into the abdomen. The ticks are transferred intoreplica plates and incubated in a climate chamber.

After 7 days egg deposition of fertile eggs is monitored. Eggs wherefertility is not visible are stored in a climate chamber till hatchingafter about 42 days. An efficacy of 100% means all eggs are infertile;0% means all eggs are fertile.

In this test, for example, the following compounds from the preparationexamples showed good activity of 100% at an application rate of 20μg/animal: I-001, I-002, I-003, I-006, I-019, I-020, I-024, I-025,I-034, I-035, I-036, I-037, I-038, I-039, I-040, I-041, I-042, I-043,I-044, I-045, I-046, I-048, I-049, I-050, I-051, I-052, I-068, I-069,I-070, I-072, I-073, I-074, I-075, I-076, I-077.

In this test, for example, the following compounds from the preparationexamples showed good activity of 80% at an application rate of 20μg/animal: I-021, I-067, I-080.

Boophilus microplus—Dip Test

Test animal: cattle ticks (Boophilus microplus) strane Parhurst,SP-resistant

Solvent: dimethyl sulfoxide

To produce a suitable preparation of active compound, 10 mg of activecompound are dissolved in 0.5 ml solvent, and the concentrate is dilutedwith water to the desired concentration.

This compound solution is pipetted into tubes. 8-10 engorged, adult,female cattle ticks (Boophilus microplus) are placed in perforatedtubes. These tubes are immersed in the aqueous compound solution untilthe ticks are completely moistened. After the liquid has drained off,the ticks are transferred to a filter paper in a plastic tray and storedin a climate chamber.

After 7 days egg deposition of fertile eggs is monitored. Eggs wherefertility is not visible are stored in a climate chamber till hatchingafter about 42 days. An efficacy of 100% means all eggs are infertile;0% means all eggs are fertile.

In this test, for example, the following compounds from the preparationexamples showed good activity of 100% at an application rate of 100 ppm:I-020, I-034, I-035, I-037, I-038, I-042, I-044, I-046.

In this test, for example, the following compounds from the preparationexamples showed good activity of 90% at an application rate of 100 ppm:I-036, I-050.

Ctenocephalides felis—Oral Test

Solvent: dimethyl sulfoxide

To produce a suitable preparation of active compound, 10 mg of activecompound are dissolved in 0.5 ml solvent, and the concentrate is dilutedwith cattle blood to the desired concentration.

Approximately 20 adult unfed cat fleas (Ctenocephalides felis) areplaced in flea chambers. The blood chamber, sealed with parafilm on thebottom, are filled with cattle blood supplied with compound solution andplaced on the gauze covered top of the flea chamber, so that the fleasare able to suck the blood. The blood chamber is heated to 37° C.whereas the flea chamber is kept at room temperature.

After 2 days mortality in % is determined. 100% means all the fleas havebeen killed; 0% means none of the fleas have been killed.

In this test, for example, the following compounds from the preparationexamples showed good activity of 100% at an application rate of 100 ppm:I-001, I-002, I-003, I-004, I-006, I-007, I-009, I-010, I-012, I-019,I-020, I-021, I-024, I-025, I-028, I-034, I-035, I-036, I-037, I-038,I-039, I-040, I-041, I-042, I-043, I-044, I-045, I-046, I-048, I-049,I-050, I-051, I-052, I-053, I-054, I-057, I-058, I-059, I-060, I-066,I-067, I-068, I-069, I-070, I-071, I-072, I-073, I-074, I-075, I-076,I-080, I-081, I-088, I-089, I-090, I-091.

In this test, for example, the following compounds from the preparationexamples showed good activity of 90% at an application rate of 100 ppm:I-056, I-077.

Diabrotica balteata—Spray Test

Solvent: 78.0 parts by weight of acetone 1.5 parts by weight ofdimethylformamide Emulsifier: alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, and theconcentrate is diluted with water, containing an emulsifierconcentration of 1000 ppm, to the desired concentration. Further testconcentrations are prepared by dilution with emulsifier containingwater.

Soaked wheat seeds (Triticum aestivum) are placed in a multiple wellplate filled with agar and some water and are incubated for 1 day togerminate (5 seeds per well). The germinated wheat seeds are sprayedwith a test solution containing the desired concentration of the activeingredient. Afterwards each unit is infected with 10-20 larvae of thebanded cucumber beetle (Diabrotica balteata).

After 7 days efficacy in % is determined. 100% means all the seedlingshave grown up like in the untreated, uninfected control; 0% means noneof the seedlings have grown.

In this test, for example, the following compounds from the preparationexamples showed good activity of 100% at an application rate of 160μg/well: I-003, I-004, I-005, I-006, I-007, I-008, I-009, I-011, I-012,I-014, I-016, I-019, I-020, I-024, I-025, I-026, I-028, I-033, I-034,I-035, I-036, I-037, I-039, I-040, I-041, I-042, I-043, I-044, I-045,I-048, I-049, I-051, I-053, I-054, I-060, I-063, I-064, I-066, I-067,I-068, I-069, I-070, I-072, I-073, I-074, I-075, I-077, I-078, I-079,I-089, I-090, I-091, I-092, I-093, I-094, I-095, I-097, I-098, I-099,I-100, I-104, I-107, I-113, I-114, I-115, I-117, I-118, I-119, I-120,I-121, I-123, I-124, I-125.

In this test, for example, the following compounds from the preparationexamples showed good activity of 80% at an application rate of 160μg/well: I-050, I-057.

Myzus persicae—Oral Test

Solvent: 100 parts by weight acetone

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, and theconcentrate is diluted with water to the desired concentration.

50 μl compound solution is filled in microtiter plates and 150 μl IPL41insect medium (33%+15% sugar) is added to obtain a total volume of 200μl per well. Afterwards the plates are sealed with parafilm throughwhich a mixed population of the green peach aphid (Myzus persicae) cansuck on the compound preparation.

After 5 days mortality in % is determined. 100% means all aphids havebeen killed and 0% means none of the aphids have been killed.

In this test, for example, the following compounds from the preparationexamples showed good activity of 100% at an application rate of 20 ppm:I-001, I-003, I-004, I-005, I-006, I-007, I-008, I-009, I-012, I-019,I-020, I-024, I-025.

In this test, for example, the following compounds from the preparationexamples showed good activity of 100% at an application rate of 4 ppm:I-007, I-008, I-009, I-019, I-020, I-024, I-033, I-034, I-035, I-036,I-037, I-038, I-039, I-040, I-041, I-042, I-043, I-044, I-046, I-048,I-050, I-051, I-057, I-063, I-067, I-069, I-070, I-074, I-075, I-080,I-090, I-091, I-092, I-095, I-096, I-097, I-099, I-117, I-119.

In this test, for example, the following compounds from the preparationexamples showed good activity of 90% at an application rate of 4 ppm:I-003, I-005, I-006, I-066, I-068, I-086, I-093, I-118.

Myzus persicae—Spray Test

Solvent: 78.0 parts by weight acetone 1.5 parts by weightdimethylformamide Emulsifier: alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvents and isdiluted with water, containing an emulsifier concentration of 1000 ppm,to the desired concentration. Further test concentrations are preparedby dilution with emulsifier containing water.

Chinese cabbage (Brassica pekinensis) leaf disks infected with allinstars of the green peach aphid (Myzus persicae), are sprayed with apreparation of the active ingredient of the desired concentration.

After 5 days mortality in % is determined. 100% means all aphids havebeen killed and 0% means none of the aphids have been killed.

In this test, for example, the following compounds from the preparationexamples showed good activity of 100% at an application rate of 500g/ha: I-036, I-039, I-04, I-044, I-045, I-046, I-050, I-070, I-092,I-099, I-121, I-124, I-125.

In this test, for example, the following compounds from the preparationexamples showed good activity of 90% at an application rate of 500 g/ha:I-034, I-035, I-037, I-040, I-042, I-043, I-057, I-066, I-073, I-074,I-075, I-091, I-095, I-096, I-100, I-114, I-118, I-119.

Nezara viridula—Spray Test

Solvent: 78.0 parts by weight of acetone 1.5 parts by weight ofdimethylformamide Emulsifier: alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, and theconcentrate is diluted with water, containing an emulsifierconcentration of 1000 ppm, to the desired concentration. Further testconcentrations are prepared by dilution with emulsifier containingwater.

Barley plants (Hordeum vulgare) infested with larvae of the southerngreen stink bug (Nezara viridula) are sprayed with a test solutioncontaining the desired concentration of the active ingredient.

After 4 days mortality in % is determined. 100% means all the stink bugshave been killed; 0% means none of the stink bugs have been killed.

In this test, for example, the following compounds from the preparationexamples showed good activity of 100% at an application rate of 500g/ha: I-001, I-002, I-003, I-004, I-005, I-006, I-007, I-008, I-016,I-019, I-020, I-025, I-033, I-034, I-035, I-036, I-037, I-038, I-039,I-040, I-041, I-042, I-043, I-044, I-045, I-046, I-049, I-050, I-051,I-057, I-060, I-063, I-066, I-067, I-068, I-069, I-070, I-073, I-074,I-075, I-078, I-080, I-089, I-090, I-091, I-092, I-093, I-095, I-096,I-097, I-098, I-099, I-100, I-104, I-107, I-110, I-117, I-118, I-119,I-120, I-121, I-124, I-125.

In this test, for example, the following compounds from the preparationexamples showed good activity of 90% at an application rate of 500 g/ha:I-109, I-113.

Nilaparvata lugens—Spray Test

Solvent: 78.0 parts by weight of acetone 1.5 parts by weight ofdimethylformamide Emulsifier: alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvents and isdiluted with water, containing an emulsifier concentration of 1000 ppm,to the desired concentration. Further test concentrations are preparedby dilution with emulsifier containing water.

Rice plants (Oryza sativa) are sprayed with a preparation of the activeingredient of the desired concentration and the plants are infested withthe brown planthopper (Nilaparvata lugens).

After 4 days mortality in % is determined. 100% means all planthoppershave been killed and 0% means none of the planthoppers have been killed.

In this test, for example, the following compounds from the preparationexamples showed good activity of 100% at an application rate of 500g/ha: I-001, I-003, I-004, I-005, I-006, I-008, I-018, I-019, I-020,I-024, I-025, I-033, I-034, I-037, I-039, I-040, I-041, I-042, I-043,I-044, I-049, I-050, I-059, I-092, I-100, I-111, I-118, I-120.

In this test, for example, the following compounds from the preparationexamples showed good activity of 90% at an application rate of 500 g/ha:I-045, I-046.

Phaedon cochleariae—Spray Test

Solvent: 78.0 parts by weight of acetone 1.5 parts by weight ofdimethylformamide Emulsifier: alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvents and isdiluted with water, containing an emulsifier concentration of 1000 ppm,to the desired concentration. Further test concentrations are preparedby dilution with emulsifier containing water.

Chinese cabbage (Brassica pekinensis) leaf disks are sprayed with apreparation of the active ingredient of the desired concentration. Oncedry, the leaf disks are infested with mustard beetle larvae (Phaedoncochleariae).

After 7 days mortality in % is determined. 100% means all beetle larvaehave been killed and 0% means none of the beetle larvae have beenkilled.

In this test, for example, the following compounds from the preparationexamples showed good activity of 100% at an application rate of 500g/ha: I-001, I-003, I-004, I-005, I-006, I-008, I-009, I-010, I-012,I-016, I-019, I-020, I-024, I-026, I-028.

In this test, for example, the following compounds from the preparationexamples showed good activity of 83% at an application rate of 500 g/ha:I-025.

Spodoptera frugiperda—Spray Test

Solvent: 78.0 parts by weight acetone 1.5 parts by weightdimethylformamide Emulsifier: alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvents and isdiluted with water, containing an emulsifier concentration of 1000 ppm,to the desired concentration. Further test concentrations are preparedby dilution with emulsifier containing water.

Maize (Zea mays) leaf sections are sprayed with a preparation of theactive ingredient of the desired concentration. Once dry, the leafsections are infested with fall armyworm larvae (Spodoptera frugiperda).

After 7 days mortality in % is determined. 100% means all caterpillarshave been killed and 0% means none of the caterpillars have been killed.

In this test, for example, the following compounds from the preparationexamples showed good activity of 100% at an application rate of 500g/ha: I-005, I-008, I-009, I-012, I-019, I-033, I-035, I-036, I-038,I-040, I-043, I-045, I-046, I-050, I-051, I-053, I-054, I-057, I-063,I-064, I-066, I-067, I-068, I-069, I-070, I-072, I-073, I-074, I-075,I-077, I-078, I-079, I-089, I-090, I-095, I-096, I-097, I-099, I-100,I-104, I-106, I-110, I-113, I-117, I-118, I-119, I-120, I-121, I-123,I-125.

In this test, for example, the following compounds from the preparationexamples showed good activity of 83% at an application rate of 500 g/ha:I-004, I-034, I-037, I-042, I-044, I-091, I-094, I-098.

Tetranychus urticae—Spray Test OP-Resistant

Solvent: 78.0 parts by weight acetone 1.5 parts by weightdimethylformamide Emulsifier: alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvents and isdiluted with water, containing an emulsifier concentration of 1000 ppm,to the desired concentration. Further test concentrations are preparedby dilution with emulsifier containing water.

French bean (Phaseolus vulgaris) leaf disks infected with all instars ofthe two spotted spidermite (Tetranychus urticae), are sprayed with apreparation of the active ingredient of the desired concentration.

After 6 days mortality in % is determined. 100% means all spider miteshave been killed and 0% means none of the spider mites have been killed.

In this test, for example, the following compounds from the preparationexamples showed good activity of 95% at an application rate of 500 g/ha:I-006, I-008.

In this test, for example, the following compounds from the preparationexamples showed good activity of 90% at an application rate of 500 g/ha:I-040, I-042, I-056, I-112.

In this test, for example, the following compounds from the preparationexamples showed good activity of 80% at an application rate of 500 g/ha:I-005.

Aedes aegypti Test (AEDSAE Surface Treatment & Contact Assay)

Solvent: Aceton+2000 ppm rapeseed oil methyl ester (RME)

In order to produce a sufficient, active ingredient containing solutionit is necessary to solve the test-compound in the solvent-mix (Acetoneat 2 mg/ml/RME 2000 ppm). This solution is pipetted onto a glazed tileand after evaporation of the Acetone, adult mosquitoes of the speciesAedes aegypti strain MONHEIM are placed onto the dried surface. Theexposure time is 30 minutes.

Mortality in percent (%) is determined 24 hours after contact to thetreated surface. 100% mortality means that all test-insects are dead,whereas 0% means that not a single insect died.

The following compound-example-numbers showed in this test efficacy of90-100% at a surface concentration of 20 mg/m²: I-001, I-019, I-024,I-025, I-034, I-035, I-036, I-037, I-038, I-040, I-041, I-042, I-043,I-044, I-045, I-046, I-048, I-049, I-050, I-053, I-054, I-057, I-063,I-066, I-067, I-068, I-069, I-070, I-073, I-074, I-075, I-077, I-078,I-089, I-091, I-092, I-093, I-098, I-100, I-104.

The following compound-example-numbers showed in this test efficacy of80-100% at a surface concentration of 4 mg/m²: I-001, I-019, I-034,I-035, I-036, I-037, I-038, I-040, I-041, I-042, I-043, I-044, I-045,I-049, I-050, I-053, I-054, I-057, I-063, I-066, I-067, I-068, I-069,I-070, I-073, I-075, I-078, I-089, I-091, I-092, I-093, I-100, I-104.

Culex quinquefasciatus Test (CULXFA Surface Treatment & Contact Assay)

Solvent: Aceton+2000 ppm rapeseed oil methyl ester (RME)

In order to produce a sufficient, active ingredient containing solutionit is necessary to solve the test-compound in the solvent-mix (Acetoneat 2 mg/ml/RME 2000 ppm). This solution is pipetted onto a glazed tileand after evaporation of the Acetone, adult mosquitoes of the speciesCulex quinquefasciatus strain P00 are placed onto the dried surface. Theexposure time is 30 minutes.

Mortality in percent (%) is determined 24 hours after contact to thetreated surface. 100% mortality means that all test-insects are dead,whereas 0% means that not a single insect died.

The following compound-example-numbers showed in this test efficacy of80-100% at a surface concentration of 20 mg/m²: I-001, I-019, I-025,I-034, I-035, I-036, I-037, I-038, I-040, I-041, I-042, I-043, I-044,I-045, I-046, I-049, I-050, I-057, I-063, I-066, I-067, I-068, I-069,I-070, I-073, I-074, I-075, I-078, I-089, I-091, I-092, I-093, I-098,I-100, I-104, I-107.

The following compound-example-numbers showed in this test efficacy of80-100% at a surface concentration of 4 mg/m²: I-019, I-034, I-035,I-036, I-037, I-038, I-040, I-041, I-042, I-043, I-044, I-045, I-050,I-063, I-066, I-067, I-068, I-069, I-070, I-073, I-075, I-078, I-089,I-091, I-092, I-093, I-100, I-104.

Anopheles funestus Test (ANPHFU Surface Treatment & Contact Assay)

Solvent: Aceton+2000 ppm rapeseed oil methyl ester (RME)

In order to produce a sufficient, active ingredient containing solutionit is necessary to solve the test-compound in the solvent-mix (Acetoneat 2 mg/ml/RME 2000 ppm). This solution is pipetted onto a glazed tileand after evaporation of the Acetone, adult mosquitoes of the speciesAnopheles funestus strain FUMOZ-R (Hunt et al., Med Vet Entomol. 2005September; 19(3):271-5) are placed onto the dried surface. The exposuretime is 30 minutes.

Mortality in percent (%) is determined 24 hours after contact to thetreated surface. 100% mortality means that all test-insects are dead,whereas 0% means that not a single insect died.

The following compound-example-numbers showed in this test efficacy of85-100% at a surface concentration of 20 mg/m²: I-001, I-024, I-025,I-041, I-042, I-045, I-049, I-066, I-068, I-070, I-073, I-078, I-091,I-100,

The following compound-example-numbers showed in this test efficacy of85-100% at a surface concentration of 4 mg/m²: I-001, I-024, I-025,I-034, I-041, I-045, I-049, I-066, I-068, I-070, I-092, I-093, I-100,

Musca domestica Test (MUSCDO Surface Treatment & Contact Assay)

Solvent: Aceton+2000 ppm rapeseed oil methyl ester (RME)

In order to produce a sufficient, active ingredient containing solutionit is necessary to solve the test-compound in the solvent-mix (Acetoneat 2 mg/ml/RME 2000 ppm). This solution is pipetted onto a glazed tileand after evaporation of the Acetone, adult flies of the species Muscadomestica strain WHO-N are placed onto the dried surface. The exposuretime is 30 minutes.

Mortality in percent (%) is determined 24 hours after contact to thetreated surface. 100% mortality means that all test-insects are dead,whereas 0% means that not a single insect died.

The following compound-example-numbers showed in this test efficacy of80-100% at a surface concentration of 20 mg/m²: I-019, I-025, I-035,I-040, I-042, I-043, I-045, I-050, I-053, I-054, I-066, I-067, I-068,I-069, I-070, I-073, I-074, I-075, I-078, I-100, I-104.

The following compound-example-numbers showed in this test efficacy of80-100% at a surface concentration of 4 mg/m²: 1-019, I-035, I-042,I-045, I-050, I-053, I-054, I-068, I-069, I-100, I-104.

Blattella germanica Test (BLTTGE Surface Treatment & Contact Assay)

Solvent: Aceton+2000 ppm rapeseed oil methyl ester (RME)

In order to produce a sufficient, active ingredient containing solutionit is necessary to solve the test-compound in the solvent-mix (Acetoneat 2 mg/ml/RME 2000 ppm). This solution is pipetted onto a glazed tileand after evaporation of the Acetone, adult animals of the speciesBlattella germanica strain PAULINIA are placed onto the dried surface.The exposure time is 30 minutes.

Mortality in percent (%) is determined 24 hours after contact to thetreated surface. 100% mortality means that all test-insects are dead,whereas 0% means that not a single insect died.

The following compound-example-numbers showed in this test efficacy of80-100% at a surface concentration of 20 mg/m²: 1-035, I-036, I-037.

1. A compound of formula (I)

wherein X is O or S; Q¹ and Q² are independently CR⁵ or N, provided atleast one of Q¹ and Q² is N; Y is a direct bond or optionallysubstituted CH₂; R¹ is hydrogen; C₁-C₆alkyl optionally substituted withone substituent selected from —CN, —CONH₂, —COOH, —NO₂ and —Si(CH₃)₃;C₁-C₆haloalkyl; C₂-C₆alkenyl; C₂-C₆haloalkenyl; C₂-C₆alkynyl;C₂-C₆haloalkynyl; C₃-C₄cycloalkyl-C₁-C₂alkyl- wherein theC₃-C₄cycloalkyl is optionally substituted with one or two halogen atoms;oxetan-3-yl-CH₂— or benzyl optionally substituted with halogen orC₁-C₃haloalkyl; R² is phenyl, pyridine, pyrimidine, pyrazine orpyridazine, wherein the phenyl, pyridine, pyrimidine, pyrazine orpyridazine is substituted with one to five substituents, provided atleast one substituent is on either carbon adjacent to the carbon bondedto the C═X group, each independently selected from the group consistingof halogen, hydroxy, —NH₂, —CN, —SF₅, —COOH, —CONH₂, —NO₂, and in eachcase optionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl,C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylthio, C₃-C₆cycloalkylsulfanyl, C₃-C₆cycloalkylsulfinyl,C₃-C₆cycloalkylsulfonyl, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl,phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, —NH(C₁-C₆alkyl),—N(C₁-C₆alkyl)₂, —NHCO—C₁-C₆alkyl, —N(C₁-C₆alkyl)CO—C₁-C₆alkyl,—NHCO-phenyl, —CO₂C₁-C₆alkyl, —CONH(C₁-C₆alkyl), —CON(C₁-C₆alkyl)₂,—CONH(C₃-C₆cycloalkyl), —CON(C₁-C₆alkyl)(C₃-C₆cycloalkyl),—C(═NOC₁-C₆alkyl)H, —C(═NOC₁-C₆alkyl)-C₁-C₆alkyl; and phenyl and 5- to6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroarylis optionally substituted with one to two substituents, eachindependently selected from the group consisting of halogen, —CN, ineach case optionally substituted C₁-C₆alkyl, C₁-C₆haloalkyl andC₁-C₆alkoxy; and an optionally substituted 4- to 6-membered saturated orpartially unsaturated heterocyclic ring; or R² is phenyl, pyridine,pyrimidine, pyrazine or pyridazine, wherein the phenyl, pyridine,pyrimidine, pyrazine or pyridazine is substituted with a total of one tothree substituents, provided the substituent(s) are not on either carbonadjacent to the carbon bonded to the C═X group and at least one and upto three substituent(s) are independently selected from group Aconsisting of optionally substituted C₄-C₆alkyl; C₁-C₆alkylthio,optionally substituted by one to three substituents independentlyselected from the group consisting of —NH₂, —OH, —NO₂, —CN, —SH,CO₂C₁-C₄alkyl, —CONH₂, SF₅, —SO₂NH₂, C₁-C₄alkyl, C₃-C₄cycloalkyl,C₂-C₄alkenyl, C₅-C₆cycloalkenyl, C₂-C₄alkynyl, —NH(C₁-C₆alkyl),—N(C₁-C₆alkyl)₂, N—C₁-C₄alkanoylamino, C₁-C₄alkoxy, C₁-C₄haloalkoxy,C₂-C₄alkenyloxy, C₂-C₄alkynyloxy, C₃-C₄cycloalkoxy,C₁-C₆cycloalkenyloxy, C₁-C₄alkoxycarbonyl, C₂-C₄alkenyloxycarbonyl,C₂-C₄alkynyloxycarbonyl, C₆—, C₁₀—, C₁₄-aryloxycarbonyl, C₁-C₄alkanoyl,C₂-C₄alkenylcarbonyl, C₂-C₄alkynylcarbonyl, C₆—, C₁₀—, C₁₄-arylcarbonyl,C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₃-C₄cycloalkylthio,C₂-C₄alkenylthio, C₅-C₆cycloalkenylthio, C₂-C₄alkynylthio,C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, C₁-C₄alkylsulfonyl,C₁-C₄haloalkylsulfonyl, —SO₂—NH(C₁-C₆alkyl), —SO₂—N(C₁-C₆alkyl)₂,C₁-C₄alkylphosphinyl, C₁-C₄alkylphosphonyl, N—C₁-C₄alkylaminocarbonyl,N,N-di-C₁-C₄alkylaminocarbonyl, N—C₁-C₄alkanoylaminocarbonyl,N—C₁-C₄alkanoyl-N—C₁-C₄alkylaminocarbonyl, C₆—, C₁₀—, C₁₄-aryl, C₆—,C₁₀—, C₁₄-aryloxy, benzyl, benzyloxy, benzylthio, C₆—, C₁₀—,C₁₄-arylthio, C₆—, C₁₀—, C₁₄-arylamino, benzylamino, heterocyclyl,heteroaryl and trialkylsilyl, substituents bonded via a double bond,such as C₁-C₄alkylidene (e.g. methylidene or ethylidene), an oxo group,an imino group and a substituted imino group; and in each caseoptionally substituted C₄-C₆haloalkylthio, C₄-C₆haloalkoxy, C₄-C₆alkoxy,C₄-C₆haloalkyl, C₃-C₆cycloalkyl, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₃-C₆cycloalkylsulfanyl, C₃-C₆cycloalkylsulfinyl,C₃-C₆cycloalkylsulfonyl, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl,C₂-C₆alkenylsulfanyl, C₂-C₆alkenylsulfinyl, C₂-C₆alkenylsulfonyl,C₂-C₆alkinylsulfanyl, C₂-C₆alkinylsulfinyl, C₂-C₆alkinylsulfonyl,phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, heterocyclylsulfanyl,heterocyclylsulfinyl, heterocyclylsulfonyl, heteroarylsulfanyl,heteroarylsulfinyl, heteroarylsulfonyl, S—C₁-C₆alkylsulfinimidoyl,S—C₃-C₆cycloalkylsulfinimidoyl, S—C₂-C₆alkenylsulfinimidoyl,S—C₂-C₆alkinylsulfinimidoyl, S-phenylsulfinimidoyl,S-heterocyclylsulfinimidoyl, S-heteroarylsulfinimidoyl,S—C₁-C₆alkylsulfonimidoyl, S—C₃-C₆cycloalkylsulfonimidoyl,S—C₂-C₆alkenylsulfonimidoyl, S—C₂-C₆alkinylsulfonimidoyl,S-phenylsulfonimidoyl, S-heterocyclylsulfonimidoyl,S-heteroarylsulfonimidoyl, —NH(C₁-C₆alkyl), —N(C₁-C₆alkyl)₂,—NHCO—C₁-C₆alkyl, —N(C₁-C₆alkyl)CO—C₁-C₆alkyl,—N(C₃-C₆cycloalkyl)CO—C₁-C₆alkyl, —NHCO-phenyl, —N(C₁-C₆alkyl)CO-phenyl,—N(C₃-C₆cycloalkyl)CO-phenyl, —NHCO—C₃-C₆cycloalkyl,—N(C₁-C₆alkyl)CO—(C₃-C₆cycloalkyl),—N(C₃-C₆cycloalkyl)CO—(C₃-C₆cycloalkyl), —NHCO-heteroaryl,—N(C₁-C₆alkyl)CO-heteroaryl, —N(C₃-C₆cycloalkyl)CO-heteroaryl,—NHCO-heterocyclyl, —N(C₁-C₆alkyl)CO-heterocyclyl,—N(C₃-C₆cycloalkyl)CO-heterocyclyl, —CO₂C₁-C₆alkyl, —CONH(C₁-C₆alkyl),—CON(C₁-C₆alkyl)₂, —CONH(C₃-C₆cycloalkyl),—CON(C₁-C₆alkyl)(C₃-C₆cycloalkyl), —CON(C₃-C₆cycloalkyl)₂, —CONH-phenyl,—CON(C₁-C₆alkyl)phenyl, —CON(C₃-C₆cycloalkyl)phenyl, —CONH-heteroaryl,—CON(C₁-C₆alkyl)heteroaryl, —CON(C₃-C₆cycloalkyl)heteroaryl,—CONH-heterocyclyl, —CON(C₁-C₆alkyl)heterocyclyl,—CON(C₃-C₆cycloalkyl)heterocyclyl, —C(═NOC₁-C₆alkyl)H,—C(═NOC₁-C₆alkyl)-C₁-C₆alkyl, —NHSO₂—C₁-C₆alkyl,—N(C₁-C₆alkyl)SO₂—C₁-C₆alkyl, —N(C₃-C₆cycloalkyl)SO₂—C₁-C₆alkyl,—NHSO₂-phenyl, —N(C₁-C₆alkyl)SO₂-phenyl, —N(C₃-C₆cycloalkyl)SO₂-phenyl,—NHSO₂—C₃-C₆cycloalkyl, —N(C₁-C₆alkyl)SO₂—(C₃-C₆cycloalkyl),—N(C₃-C₆cycloalkyl)SO₂—(C₃-C₆cycloalkyl), —NHSO₂-heterocyclyl,—N(C₁-C₄alkyl)SO₂-heterocyclyl, —N(C₃-C₆cycloalkyl)SO₂-heterocyclyl,—NHSO₂-heteroaryl, —N(C₁-C₆alkyl)SO₂-heteroaryl,—N(C₃-C₆cycloalkyl)SO₂-heteroaryl, —SO₂NH(C₁-C₆alkyl),—SO₂N(C₁-C₆alkyl)₂, —SO₂N(C₁-C₆alkyl)(C₃-C₆cycloalkyl),—SO₂NH(C₃-C₆cycloalkyl), —SO₂N(C₃-C₆cycloalkyl)₂, —SO₂NH(phenyl),—SO₂N(C₁-C₆alkyl)(phenyl), —SO₂N(C₁-C₄cycloalkyl)(phenyl),—SO₂NH(heteroaryl), —SO₂N(C₁-C₆alkyl)(heteroaryl),—SO₂N(C₃-C₆cycloalkyl)(heteroaryl), —SO₂NH(heterocyclyl),—SO₂N(C₁-C₄alkyl)(heterocyclyl), —SO₂N(C₃-C₆cycloalkyl)(heterocyclyl);and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl or 5- to6-membered heteroaryl is optionally substituted with one to twosubstituents, each independently selected from the group consisting ofhalogen, —CN, in each case optionally substituted C₁-C₆alkyl,C₁-C₆haloalkyl, C₁-C₆alkoxy and C₁-C₆haloalkoxy; and an optionallysubstituted 4- to 6-membered saturated or partially unsaturatedheterocyclic ring; and —SO₂NH₂; and the other one to two optionalsubstituent(s) are each independently selected from group B consistingof halogen, hydroxy, —NH₂, —CN, —SF₅, —COOH, —CONH₂, —NO₂, and in eachcase optionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl,C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl,phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, —NH(C₁-C₆alkyl),—N(C₁-C₆alkyl)₂, —NHCO—C₁-C₆alkyl, —N(C₁-C₆alkyl)CO—C₁-C₆alkyl,—NHCO-phenyl, —CO₂C₁-C₆alkyl, —CONH(C₁-C₆alkyl), —CON(C₁-C₆alkyl)₂,—CONH(C₃-C₆cycloalkyl), —CON(C₁-C₆alkyl)(C₃-C₆cycloalkyl),—C(═NOC₁-C₆alkyl)H, —C(═NOC₁-C₆alkyl)-C₁-C₆alkyl; and phenyl and 5- to6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroarylis optionally substituted with one to two substituents, eachindependently selected from the group consisting of halogen, —CN, ineach case optionally substituted C₁-C₆alkyl, C₁-C₆haloalkyl andC₁-C₆alkoxy; or R² is naphthyl optionally substituted by one to threesubstituents independently selected from the group consisting ofhalogen, hydroxy, —CN, —COOH, —CONH₂, —NO₂, —SF₅, —NH₂, and in each caseoptionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl,C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₃-C₆cycloalkylsulfanyl, C₃-C₆cycloalkylsulfinyl,C₃-C₆cycloalkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl,C₁-C₆haloalkylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl,—NH(C₁-C₆alkyl), —N(C₁-C₆alkyl)₂, —NHCO—C₁-C₆alkyl,—N(C₁-C₆alkyl)CO—C₁-C₆alkyl, —NHCO-phenyl, —CO₂C₁-C₆alkyl,—CONH(C₁-C₆alkyl), —CON(C₁-C₆alkyl)₂, —C(═NOC₁-C₆alkyl)H,—C(═NOC₁-C₆alkyl)-C₁-C₆alkyl; and phenyl and 5- to 6-memberedheteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl isoptionally substituted with one to two substituents, each independentlyselected from the group consisting of halogen, —CN, in each caseoptionally substituted C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy; or R²is a heterocyclic ring which is selected from the group consisting of 4-to 10-membered saturated and partially unsaturated heterocyclyl,5-membered heteroaryl, 9-membered heteroaryl and 10-membered heteroaryl,each of which is optionally substituted by one to three substituentsindependently selected from the group consisting of halogen, ═O (oxo),hydroxy, —CN, —COOH, —CONH₂, —NO₂, —SF₅, —NH₂, and in each caseoptionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl,C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₃-C₆cycloalkylsulfanyl, C₃-C₆cycloalkylsulfinyl,C₃-C₆cycloalkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl,C₁-C₆haloalkylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl,—NH(C₁-C₆alkyl), —N(C₁-C₆alkyl)₂, —NHCO—C₁-C₆alkyl,—N(C₁-C₆alkyl)CO—C₁-C₆alkyl, —NHCO-phenyl, —CO₂C₁-C₆alkyl,—CONH(C₁-C₆alkyl), —CON(C₁-C₆alkyl)₂, —C(═NOC₁-C₆alkyl)H,—C(═NOC₁-C₆alkyl)-C₁-C₆alkyl; and phenyl and 5- to 6-memberedheteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl isoptionally substituted with one to two substituents, each independentlyselected from the group consisting of halogen, —CN, in each caseoptionally substituted C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy; or R²is in each case optionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl orC₁-C₆haloalkyl; R^(3a), R^(3b) are independently selected from the groupconsisting of hydrogen; halogen; —CN; C₁-C₆alkyl optionally substitutedby one to three substituents independently selected from the groupconsisting of halogen, hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, in eachcase optionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy,C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, —NH(C₁-C₆alkyl),—N(C₁-C₆alkyl)₂, —NHCO—C₁-C₆alkyl, —N(C₁-C₆alkyl)CO—C₁-C₆alkyl,—CO₂C₁-C₆alkyl, —CONH(C₁-C₆alkyl), and —CON(C₁-C₆alkyl)₂; optionallysubstituted C₃-C₆cycloalkyl; optionally substituted C₁-C₆haloalkyl;optionally substituted C₂-C₆alkenyl; optionally substitutedC₂-C₆haloalkenyl; optionally substituted C₂-C₆alkynyl; benzyl whereinthe phenyl substituent is optionally substituted with one to fivesubstituents, each independently selected from the group consisting ofhalogen, hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, —SF₅, in each caseoptionally substituted C₁-C₆alkyl, C₁-C₆alkoxy, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, and C₁-C₆alkylsulfonyl; heterocyclyl-C₁-C₆alkylwherein the heterocyclyl substituent is selected from the groupconsisting of 4- to 10-membered saturated and partially unsaturatedheterocyclyl, 5-membered heteroaryl and 6-membered heteroaryl, each ofwhich is optionally substituted by one to three substituentsindependently selected from the group consisting of halogen, ═O (oxo),hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, in each case optionallysubstituted C₁-C₆alkyl, and C₁-C₆alkoxy; phenyl optionally substitutedwith one to five substituents, each independently selected from thegroup consisting of halogen, hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂,—SF₅, in each case optionally substituted C₁-C₆alkyl, C₁-C₆alkoxy,C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, and C₁-C₆alkylsulfonyl; orheterocyclyl wherein the heterocyclyl substituent is selected from thegroup consisting of 4- to 10-membered saturated and partiallyunsaturated heterocyclyl, 5-membered heteroaryl and 6-memberedheteroaryl, each of which is optionally substituted by one to threesubstituents independently selected from the group consisting ofhalogen, ═O (oxo), hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, in each caseoptionally substituted C₁-C₆alkyl, and C₁-C₆alkoxy; or R^(3a), R^(3b)form together with the carbon to which they are connected aC₃-C₆-carbocyclic or 3- to 6-membered heterocyclic ring system,optionally substituted with one to two substituents, each independentlyselected from the group consisting of halogen, —CN, in each caseoptionally substituted C₁-C₆alkyl, C₁-C₆alkoxy and C₁-C₆haloalkoxy; R⁴is pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl,wherein the pyridine, pyrimidine, pyrazine, pyridazine or 5-memberedheteroaryl is optionally substituted with one to three substituentsselected from the group consisting of halogen, hydroxy, —CN, —COOH,—CO₂—C₁-C₆alkyl, —SO₂NH₂, —CONH₂, —CSNH₂, —NO₂, —NH₂, in each caseoptionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl,C₁-C₆haloalkylsulfonyl, C₃-C₆cycloalkylsulfanyl,C₃-C₆cycloalkylsulfinyl, C₃-C₆cycloalkylsulfonyl, C₂-C₄alkenylsulfanyl,C₂-C₄alkenylsulfinyl, C₂-C₄alkenylsulfonyl, C₂-C₄alkinylsulfanyl,C₂-C₄alkinylsulfinyl, C₂-C₄alkinylsulfonyl, phenylsulfanyl,phenylsulfinyl, phenylsulfonyl, S—C₁-C₆alkylsulfinimidoyl,S—C₃-C₆cycloalkylsulfinimidoyl, S—C₂-C₆alkenylsulfinimidoyl,S—C₂-C₆alkinylsulfinimidoyl, S-phenylsulfinimidoyl,S—C₁-C₆alkylsulfonimidoyl, S—C₃-C₆cycloalkylsulfonimidoyl,S—C₂-C₆alkenylsulfonimidoyl, S—C₂-C₆alkinylsulfonimidoyl,S-phenylsulfonimidoyl, —NH(C₁-C₆alkyl), —N(C₁-C₆alkyl)₂,—NHCO—C₁-C₆alkyl, —N(C₁-C₆alkyl)CO—C₁-C₆alkyl,—N(C₃-C₆cycloalkyl)CO—C₁-C₆alkyl, —NHCO—C₃-C₆cycloalkyl,—N(C₁-C₆alkyl)CO—(C₃-C₆cycloalkyl),—N(C₃-C₆cycloalkyl)CO—(C₃-C₆cycloalkyl), —N(C₁-C₆alkyl)CO-phenyl,—N(C₃-C₆cycloalkyl)CO-phenyl, —NHCO-phenyl, —N(CO—C₁-C₆alkyl)₂,—N(CO—C₃-C₆cycloalkyl)₂, —N(CO-phenyl)₂,—N(CO—C₃-C₆cycloalkyl)(CO—C₁-C₆alkyl),—N(CO—C₃-C₆cycloalkyl)(CO-phenyl), —N(CO—C₁-C₆alkyl)(CO-phenyl),—CONH(C₁-C₆alkyl), —CON(C₁-C₆alkyl)₂, —CONH(C₃-C₆cycloalkyl),—CON(C₁-C₆alkyl)(C₃-C₆cycloalkyl), —CON(C₃-C₆cycloalkyl)₂,—CONH—SO₂—C₁-C₆alkyl, —CONH—SO₂-phenyl, —CONH—SO₂—(C₃-C₆cycloalkyl),—CON(C₁-C₆alkyl)-SO₂—C₁-C₆alkyl, —CON(C₁-C₆alkyl)-SO₂-phenyl,—CON(C₁-C₆alkyl)-SO₂—(C₃-C₆cycloalkyl), —CONH-phenyl,—CON(C₁-C₆alkyl)phenyl, —CON(C₃-C₆cycloalkyl)phenyl, —N(SO₂C₁-C₆alkyl)₂,—N(SO₂C₁-C₆haloalkyl)₂, —N(SO₂C₃-C₆cycloalkyl)₂,—N(SO₂C₁-C₆alkyl)SO₂-phenyl, —N(SO₂C₃-C₆cycloalkyl)SO₂-phenyl,—NHSO₂—C₁-C₆alkyl, —NHSO₂—C₁-C₆haloalkyl, —N(C₁-C₆alkyl)SO₂—C₁-C₆alkyl,—N(C₃-C₆cycloalkyl)SO₂—C₁-C₆alkyl, —NHSO₂-phenyl,—N(C₁-C₆alkyl)SO₂-phenyl, —N(C₃-C₆cycloalkyl)SO₂-phenyl,—NHSO₂—C₃-C₆cycloalkyl, —N(C₁-C₆alkyl)SO₂—(C₃-C₆cycloalkyl),—N(C₃-C₆cycloalkyl)SO₂—(C₃-C₆cycloalkyl), —SO₂NH(C₁-C₆alkyl),—SO₂N(C₁-C₆alkyl)₂, —SO₂N(C₁-C₆alkyl)(C₃-C₆cycloalkyl),—SO₂NH(C₃-C₆cycloalkyl), —SO₂N(C₃-C₆cycloalkyl)₂, —SO₂NH(phenyl),—SO₂N(C₁-C₆alkyl)(phenyl), —SO₂N(C₁-C₄cycloalkyl)(phenyl),—C(═NOC₁-C₆alkyl)H and —C(═NOC₁-C₆alkyl)-C₁-C₆alkyl; R⁵ is hydrogen,halogen, —CN, or in each case optionally substituted C₁-C₆alkyl,C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆alkoxyC(O)—, (C₁-C₆alkoxy)₂CH—,—CO₂C₁-C₆alkyl, —CONH(C₁-C₆alkyl), —CON(C₁-C₆alkyl)₂, —NHCO—C₁-C₆alkyl,—N(C₁-C₆alkyl)CO—C₁-C₆alkyl, —C(═NOC₁-C₆alkyl)H, or—C(═NOC₁-C₆alkyl)-C₁-C₆alkyl.
 2. The compound according to claim 1,wherein X is O or S; Q¹ and Q² are independently CR⁵ or N, provided atleast one of Q¹ and Q² is N; Y is a direct bond or CH₂; R¹ is hydrogen;C₁-C₆alkyl optionally substituted with one substituent selected from—CN, —CONH₂, —COOH, —NO₂ and —Si(CH₃)₃; C₁-C₆haloalkyl; C₂-C₆alkenyl;C₂-C₆haloalkenyl; C₂-C₆alkynyl; C₂-C₆haloalkynyl;C₃-C₄cycloalkyl-C₁-C₂alkyl- wherein the C₃-C₄cycloalkyl is optionallysubstituted with one or two halogen atoms; oxetan-3-yl-CH₂—; or benzyloptionally substituted with halogen or C₁-C₃haloalkyl; R² is phenyl,pyridine, pyrimidine, pyrazine or pyridazine, wherein the phenyl,pyridine, pyrimidine, pyrazine or pyridazine is substituted with one tofive substituents, provided at least one substituent is on either carbonadjacent to the carbon bonded to the C═X group, each independentlyselected from the group consisting of halogen, hydroxy, —NH₂, —CN, —SF₅,—COOH, —CONH₂, —NO₂, C₁-C₆alkyl, optionally substituted C₃-C₆cycloalkyl;C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy,C₁-C₃haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₃-C₆cycloalkylsulfanyl, C₃-C₆cycloalkylsulfinyl,C₃-C₆cycloalkylsulfonyl, C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl,C₁-C₃haloalkylsulfonyl; phenylsulfanyl, phenylsulfinyl, phenylsulfonyl,wherein in each case the phenyl is optionally substituted with one totwo substituents selected from the group consisting of halogen, CN,C₁-C₆alkyl and C₁-C₃haloalkyl; —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂,—NHCO—C₁-C₄alkyl, —N(C₁-C₄alkyl)CO—C₁-C₄alkyl; —NHCO-phenyl, wherein thephenyl is optionally substituted with one to two substituents selectedfrom the group consisting of halogen, CN, C₁-C₆alkyl and C₁-C₃haloalkyl;—CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂,—CONH(C₃-C₆cycloalkyl), —CON(C₁-C₄alkyl)(C₃-C₆cycloalkyl),—C(═NOC₁-C₄alkyl)H, —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl; and phenyl and 5- to6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroarylis optionally substituted with one to two substituents, eachindependently selected from the group consisting of halogen, —CN,C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy; or R² is phenyl, pyridine,pyrimidine, pyrazine or pyridazine, wherein the phenyl, pyridine,pyrimidine, pyrazine or pyridazine is substituted with a total of one tothree substituents, provided the substituent(s) are not on either carbonadjacent to the carbon bonded to the C═X group and at least one and upto three substituent(s) are independently selected from group Aconsisting of C₄-C₆-alkyl, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,C₁-C₆alkylsulfonyl, C₃-C₆cycloalkylsulfanyl, C₃-C₆cycloalkylsulfinyl,C₃-C₆cycloalkylsulfonyl, C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl;phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, wherein in each case thephenyl is optionally substituted with one to two substituents selectedfrom the group consisting of halogen, CN, C₁-C₆alkyl and C₁-C₃haloalkyl;optionally substituted C₃-C₆cycloalkyl; —NH(C₁-C₄alkyl),—N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl, —N(C₁-C₄alkyl)CO—C₁-C₄alkyl,—NHCO—C₃-C₄cycloalkyl, —NHSO₂-phenyl; —NHCO-phenyl, wherein the phenylis optionally substituted with one to two substituents selected from thegroup consisting of halogen, —CN, C₁-C₆alkyl and C₁-C₃haloalkyl;—CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂,—CONH(C₃-C₆cycloalkyl), —CON(C₁-C₄alkyl)(C₃-C₆cycloalkyl),—C(═NOC₁-C₄alkyl)H, —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl; and phenyl and 5- to6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroarylis optionally substituted with one to two substituents, eachindependently selected from the group consisting of halogen, —CN,C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy and C₁-C₄haloalkoxy; and theother one to two optional substituent(s) are each independently selectedfrom group B consisting of halogen, hydroxy, —NH₂, —CN, —SF₅, —COOH,—CONH₂, —NO₂, C₁-C₆alkyl, optionally substituted C₃-C₆cycloalkyl;C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy,C₁-C₃haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl;phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, wherein in each case thephenyl is optionally substituted with one to two substituents selectedfrom the group consisting of halogen, CN, C₁-C₆alkyl and C₁-C₃haloalkyl;—NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl,—N(C₁-C₄alkyl)CO—C₁-C₄alkyl; —NHCO-phenyl, wherein the phenyl isoptionally substituted with one to two substituents selected from thegroup consisting of halogen, CN, C₁-C₆alkyl and C₁-C₃haloalkyl;—CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂,—CONH(C₃-C₆cycloalkyl), —CON(C₁-C₄alkyl)(C₃-C₆cycloalkyl),—C(═NOC₁-C₄alkyl)H, —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl; and phenyl and 5- to6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroarylis optionally substituted with one to two substituents, eachindependently selected from the group consisting of halogen, —CN,C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy; or R² is naphthyl optionallysubstituted by one to three substituents independently selected from thegroup consisting of halogen, hydroxy, —CN, —COOH, —CONH₂, —NO₂, —SF₅,—NH₂, C₁-C₆alkyl, optionally substituted C₃-C₆cycloalkyl;C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy,C₁-C₃haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₃-C₆cycloalkylsulfanyl, C₃-C₆cycloalkylsulfinyl,C₃-C₆cycloalkylsulfonyl, C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl,C₁-C₃haloalkylsulfonyl; phenylsulfanyl, phenylsulfinyl, phenylsulfonyl,wherein in each case the phenyl is optionally substituted with one totwo substituents selected from the group consisting of halogen, CN,C₁-C₆alkyl and C₁-C₃haloalkyl; —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂,—NHCO—C₁-C₄alkyl, —N(C₁-C₄alkyl)CO—C₁-C₄alkyl; —NHCO-phenyl, wherein thephenyl is optionally substituted with one to two substituents selectedfrom the group consisting of halogen, CN, C₁-C₆alkyl and C₁-C₃haloalkyl;—CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂,—C(═NOC₁-C₄alkyl)H, —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl; and phenyl and 5- to6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroarylis optionally substituted with one to two substituents, eachindependently selected from the group consisting of halogen, —CN,C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy; or R² is a heterocyclic ringwhich is selected from the group consisting of 4- to 10-memberedsaturated and partially unsaturated heterocyclyl, 5-membered heteroaryl,9-membered heteroaryl and 10-membered heteroaryl, each of which isoptionally substituted by one to three substituents independentlyselected from the group consisting of halogen, ═O (oxo), hydroxy, —CN,—COOH, —CONH₂, —NO₂, —SF₅, —NH₂, C₁-C₆alkyl, optionally substitutedC₃-C₆cycloalkyl; C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₃haloalkyl,C₁-C₄alkoxy, C₁-C₃haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,C₁-C₆alkylsulfonyl, C₃-C₆cycloalkylsulfanyl, C₃-C₆cycloalkylsulfinyl,C₃-C₆cycloalkylsulfonyl, C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl,C₁-C₃haloalkylsulfonyl; phenylsulfanyl, phenylsulfinyl, phenylsulfonyl,wherein in each case the phenyl is optionally substituted with one totwo substituents selected from the group consisting of halogen, CN,C₁-C₆alkyl and C₁-C₃haloalkyl; —NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂,—NHCO—C₁-C₄alkyl, —N(C₁-C₄alkyl)CO—C₁-C₄alkyl; —NHCO-phenyl, wherein thephenyl is optionally substituted with one to two substituents selectedfrom the group consisting of halogen, CN, C₁-C₆alkyl and C₁-C₃haloalkyl;—CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂,—C(═NOC₁-C₄alkyl)H, —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl; and phenyl and 5- to6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroarylis optionally substituted with one to two substituents, eachindependently selected from the group consisting of halogen, —CN,C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy; or R² is C₁-C₆alkylsubstituted with one substituent selected from the group consisting ofC₁-C₃alkoxy-, C₁-C₃haloalkoxy-, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,C₁-C₆alkylsulfonyl, C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl,C₁-C₃haloalkylsulfonyl; phenyl and 5- to 6-membered heteroaryl, whereinthe phenyl or 5- to 6-membered heteroaryl is optionally substituted withone to two substituents, each independently selected from the groupconsisting of halogen, —CN, C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy;C₃-C₆cycloalkyl optionally substituted with one to two substituentsselected from the group consisting of halogen, —CN, —COOH, —CONH₂,C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy,—CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), and —CON(C₁-C₄alkyl)₂; andC₁-C₆haloalkyl; R^(3a), R^(3b) are independently selected from the groupconsisting of hydrogen; halogen; —CN; C₁-C₆alkyl optionally substitutedby one to three substituents independently selected from the groupconsisting of hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, C₁-C₆alkyl,C₃-C₆cycloalkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₃haloalkoxy,C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl,—NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl,—N(C₁-C₄alkyl)CO—C₁-C₄alkyl, —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), and—CON(C₁-C₄alkyl)₂; C₃-C₆cycloalkyl optionally substituted with one totwo substituents selected from the group consisting of halogen, —CN,—COOH, —CONH₂, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, —CO₂C₁-C₄alkyl, —CONH(C₁-C₄alkyl), and—CON(C₁-C₄alkyl)₂; C₁-C₆haloalkyl optionally substituted with one to twosubstituents selected from the group consisting of hydroxy, —CN,C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, —CO₂C₁-C₄alkyl,—CONH(C₁-C₄alkyl), and —CON(C₁-C₄alkyl)₂; C₂-C₆alkenyl;C₂-C₆haloalkenyl; C₂-C₆alkynyl; C₂-C₆haloalkynyl; benzyl wherein thephenyl substituent is optionally substituted with one to fivesubstituents, each independently selected from the group consisting ofhalogen, hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, —SF₅, C₁-C₆alkyl,C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₃alkylthio,C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, C₁-C₃haloalkylthio,C₁-C₃haloalkylsulfinyl, and C₁-C₃haloalkylsulfonyl;heterocyclyl-C₁-C₆alkyl wherein the heterocyclyl substituent is selectedfrom the group consisting of 4- to 10-membered saturated and partiallyunsaturated heterocyclyl, 5-membered heteroaryl and 6-memberedheteroaryl, each of which is optionally substituted by one to threesubstituents independently selected from the group consisting ofhalogen, ═O (oxo), hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, C₁-C₆alkyl,C₁-C₃haloalkyl and C₁-C₄alkoxy; phenyl optionally substituted with oneto five substituents, each independently selected from the groupconsisting of halogen, hydroxy, —CN, —COOH, —CONH₂, —N₂, —NH₂, —SF₅,C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy,C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, and C₁-C₃haloalkylsulfonyl;and heterocyclyl wherein the heterocyclyl substituent is selected fromthe group consisting of 4- to 10-membered saturated and partiallyunsaturated heterocyclyl, 5-membered heteroaryl and 6-memberedheteroaryl, each of which is optionally substituted by one to threesubstituents independently selected from the group consisting ofhalogen, ═O (oxo), hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, C₁-C₆alkyl,C₁-C₃haloalkyl and C₁-C₄alkoxy; or R^(3a), R^(3b) form together with thecarbon to which they are connected a C₃-C₆-carbocyclic or 3- to6-membered heterocyclic ring system, optionally substituted with one totwo substituents, each independently selected from the group consistingof halogen, —CN, C₁-C₆alkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy andC₁-C₃haloalkoxy; R⁴ is pyridine, pyrimidine, pyrazine, pyridazine or5-membered heteroaryl, wherein the pyridine, pyrimidine, pyrazine,pyridazine or 5-membered heteroaryl is optionally substituted with oneto three substituents selected from the group consisting of halogen,hydroxy, —CN, —COOH, —CO₂—C₁-C₆alkyl, —CONH₂, —CSNH₂, —NO₂, —NH₂,C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy,C₁-C₃haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl,—NH(C₁-C₄alkyl), —N(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl, wherein the alkyl isoptionally substituted with —CN, C₁-C₆alkyl and C₁-C₄alkoxy;—NHCO—C₁-C₄haloalkyl, —NHCO—C₃-C₆cycloalkyl, wherein the cycloalkyl isoptionally substituted with one to two substituents selected from thegroup consisting of halogen, —CN, C₁-C₆alkyl or C₁-C₄alkoxy;—NHCO-phenyl, wherein the phenyl is optionally substituted with one totwo substituents selected from the group consisting of halogen, —CN,C₁-C₆alkyl and C₁-C₃haloalkyl; —N(C₁-C₄alkyl)CO—C₁-C₄alkyl,—N(C₁-C₄alkyl)CO—C₃-C₆cycloalkyl; —N(C₁-C₄alkyl)CO-phenyl, wherein thephenyl is optionally substituted with one to two substituents selectedfrom the group consisting of halogen, CN, C₁-C₆alkyl and C₁-C₃haloalkyl;—N(SO₂C₁-C₃alkyl)₂, —NH(SO₂C₁-C₃alkyl), —N(C₁-C₄alkyl)(SO₂C₁-C₃alkyl),—N(SO₂C₁-C₃haloalkyl)₂, —NH(SO₂C₁-C₃haloalkyl), —CONH(C₁-C₄alkyl),—CON(C₁-C₄alkyl)₂, —CONH—SO₂—C₁-C₃alkyl,—CON(C₁-C₄alkyl)(C₃-C₆cycloalkyl), —CONH(C₁-C₄haloalkyl),—CONH(C₃-C₆cycloalkyl), —CONH(C₃-C₆cyanocycloalkyl), —C(═NOC₁-C₄alkyl)Hand —C(═NOC₁-C₄alkyl)-C₁-C₄alkyl; and —CONH-phenyl, wherein the phenylis optionally substituted with one to two substituents, eachindependently selected from the group consisting of halogen, —CN,C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy; R⁵ is hydrogen, halogen,—CN, C₁-C₃alkyl, C₁-C₃haloalkyl, C₃-C₄cycloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkoxyC(O)—, (C₁-C₃alkoxy)₂CH—, —CO₂C₁-C₄alkyl,—CONH(C₁-C₄alkyl), —CON(C₁-C₄alkyl)₂, —NHCO—C₁-C₄alkyl,—N(C₁-C₄alkyl)CO—C₁-C₄alkyl, —C(═NOC₁-C₄alkyl)H, or—C(═NOC₁-C₄alkyl)-C₁-C₄alkyl.
 3. The compound according to claim 1,wherein X is O or S; Q¹ and Q² are independently CR⁵ or N, provided atleast one of Q¹ and Q² is N; Y is a direct bond or CH₂; R¹ is hydrogen;C₁-C₃alkyl optionally substituted with one substituent selected from—CN, —CONH₂, —COOH, —NO₂ and —Si(CH₃)₃; C₁-C₃haloalkyl; C₂-C₄alkenyl;C₂-C₄haloalkenyl; C₂-C₄alkynyl; C₂-C₄haloalkynyl;C₃-C₄cycloalkyl-C₁-C₂alkyl- wherein the C₃-C₄cycloalkyl is optionallysubstituted with one or two halogen atoms; oxetan-3-yl-CH₂—; or benzyloptionally substituted with halogen or C₁-C₃haloalkyl; R² is phenyl,pyridine, pyrimidine, pyrazine or pyridazine, wherein the phenyl,pyridine, pyrimidine, pyrazine or pyridazine is substituted with one tofive substituents, provided at least one substituent is on either carbonadjacent to the carbon bonded to the C═X group, each independentlyselected from the group consisting of halogen, —CN, —NO₂, C₁-C₆alkyl,C₃-C₆cycloalkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₃haloalkoxy,C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,C₃-C₄cycloalkylsulfanyl, C₃-C₄cycloalkylsulfinyl,C₃-C₄cycloalkylsulfonyl, C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl,C₁-C₃haloalkylsulfonyl; and phenyl and 5- to 6-membered heteroaryl,wherein the phenyl or 5- to 6-membered heteroaryl is optionallysubstituted with one to two substituents selected from the groupconsisting of halogen, —CN, C₁-C₃alkyl and C₁-C₃haloalkyl; or R² isphenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein thephenyl, pyridine, pyrimidine, pyrazine or pyridazine is substituted witha total of one to three substituents, provided the substituent(s) arenot on either carbon adjacent to the carbon bonded to the C═X group andat least one and up to two substituent(s) are independently selectedfrom group A consisting of C₄-alkyl, C₃-C₄cycloalkyl, wherein theC₃-C₄cycloalkyl is optionally substituted with —CN or halogen,C₁-C₄alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,C₃-C₄cycloalkylsulfanyl, C₃-C₄cycloalkylsulfinyl,C₃-C₄cycloalkylsulfonyl, C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl;and phenylsulfanyl wherein the phenyl is optionally substituted with oneto two substituents selected from the group consisting of halogen, —CN,C₁-C₃alkyl and C₁-C₃haloalkyl; phenylsulfinyl wherein the phenyl isoptionally substituted with one to two substituents selected from thegroup consisting of halogen, —CN, C₁-C₃alkyl and C₁-C₃haloalkyl;phenylsulfonyl wherein the phenyl is optionally substituted with one totwo substituents selected from the group consisting of halogen, —CN,C₁-C₃alkyl and C₁-C₃haloalkyl; —NHCO-phenyl, wherein the phenyl isoptionally substituted with one to two substituents selected from thegroup consisting of halogen, CN, C₁-C₆alkyl and C₁-C₃haloalkyl;—NHCO—C₁-C₃alkyl, —NHCO—C₃-C₄cycloalkyl, —NHSO₂-phenyl;—CONH(C₃-C₄cycloalkyl), —CON(C₁-C₃alkyl)(C₃-C₄cycloalkyl),—C(═NOC₁-C₃alkyl)-C₁-C₃alkyl; and phenyl and 5- to 6-memberedheteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl isoptionally substituted with one to two substituents selected from thegroup consisting of halogen, —CN, C₁-C₃alkyl, C₁-C₃haloalkyl andC₁-C₃haloalkoxy; and the other one to two optional substituent(s) areeach independently selected from group B consisting of halogen, —CN,—NO₂, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl; andphenyl and 5- to 6-membered heteroaryl, wherein the phenyl and 5- to6-membered heteroaryl is optionally substituted with one to twosubstituents selected from the group consisting of halogen, —CN,C₁-C₃alkyl and C₁-C₃haloalkyl; or R² is thiophene, furane, pyrazole,thiazole, isothiazole, oxazole or isoxazole each of which is optionallysubstituted by one to three substituents independently selected from thegroup consisting of halogen, hydroxy, —CN, —NO₂, C₁-C₆alkyl,C₃-C₄cycloalkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₃haloalkoxy,C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,C₃-C₄cycloalkylsulfanyl, C₃-C₄cycloalkylsulfinyl,C₃-C₄cycloalkylsulfonyl, C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl,C₁-C₃haloalkylsulfonyl; and phenyl and 5- to 6-membered heteroaryl,wherein the phenyl or 5- to 6-membered heteroaryl is optionallysubstituted with one to two substituents selected from the groupconsisting of halogen, —CN, C₁-C₃alkyl and C₁-C₃haloalkyl or R² isC₁-C₆alkyl substituted with one substituent selected from the groupconsisting of C₁-C₃alkoxy-, C₁-C₃haloalkoxy-, C₁-C₃alkylthio,C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, C₁-C₃haloalkylthio,C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl; and phenyl, wherein thephenyl is optionally substituted with one to two substituents, eachindependently selected from the group consisting of halogen, —CN,C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy; or R² is naphthyl optionallysubstituted by one to three substituents independently selected from thegroup consisting of halogen, hydroxy, —CN, —NO₂, C₁-C₆alkyl,C₃-C₄cycloalkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₃haloalkoxy,C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,C₃-C₄cycloalkylsulfanyl, C₃-C₄cycloalkylsulfinyl,C₃-C₄cycloalkylsulfonyl, C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl,C₁-C₃haloalkylsulfonyl; and phenyl and 5- to 6-membered heteroaryl,wherein the phenyl or 5- to 6-membered heteroaryl is optionallysubstituted with one to two substituents selected from the groupconsisting of halogen, —CN, C₁-C₃alkyl and C₁-C₃haloalkyl or R² is a9-membered or 10-membered heteroaryl, which is optionally substituted byone to three substituents independently selected from the groupconsisting of halogen, hydroxy, —CN, —NO₂, C₁-C₆alkyl, C₃-C₄cycloalkyl,C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio,C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, C₃-C₄cycloalkylsulfanyl,C₃-C₄cycloalkylsulfinyl, C₃-C₄cycloalkylsulfonyl, C₁-C₃haloalkylthio,C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl; and phenyl and 5- to6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroarylis optionally substituted with one to two substituents selected from thegroup consisting of halogen, —CN, C₁-C₃alkyl and C₁-C₃haloalkyl; R^(3a),R^(3b) are independently selected from the group consisting of hydrogen;C₁-C₆alkyl optionally substituted by one to three substituentsindependently selected from the group consisting of C₁-C₆alkyl,C₃-C₆cycloalkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₃haloalkoxy,C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, and C₁-C₃haloalkylsulfonyl;C₃-C₆cycloalkyl; C₁-C₆haloalkyl; C₂-C₆alkenyl; C₂-C₆haloalkenyl;C₂-C₆alkynyl; C₂-C₆haloalkynyl; benzyl wherein the phenyl substituent isoptionally substituted with one to three substituents independentlyselected from the group consisting of halogen, —CN, —NO₂, C₁-C₆alkyl,C₁-C₃haloalkyl, C₁-C₄alkoxy, and C₁-C₄haloalkoxy; orheterocyclyl-C₁-C₆alkyl wherein the heterocyclyl substituent is selectedfrom the group consisting of 4- to 10-membered heterocyclyl, 5-memberedheteroaryl and 6-membered heteroaryl, each of which is optionallysubstituted by one to three substituents independently selected from thegroup consisting of halogen, —CN, —NO₂, C₁-C₆alkyl, C₁-C₃haloalkyl, andC₁-C₄alkoxy; or phenyl optionally substituted with one substituentselected from the group consisting of halogen, —CN, —NO₂, C₁-C₆alkyl,C₁-C₃haloalkyl and C₁-C₄alkoxy; or R^(3a), R^(3b) form together with thecarbon to which they are connected a cyclopropane, cyclobutane, oxetaneor tetrahydropyrane ring optionally substituted with one to twosubstituents, each independently selected from the group consisting ofhalogen, —CN, C₁-C₆alkyl, C₁-C₃haloalkyl and C₁-C₄alkoxy; R⁴ ispyridine, pyrimidine, pyrazine, pyridazine or thiazole, wherein (A) thepyridine, pyrimidine, pyrazine or pyridazine is optionally substitutedwith one to three substituents selected from the group consisting ofhalogen, —CN, —NH₂, —NO₂, —COOH, —CONH₂, —CSNH₂, —CO₂—C₁-C₃alkyl,C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl, C₁-C₃haloalkylsulfonyl,—NHCO—C₁-C₃alkyl, —NHCO—C₁-C₃haloalkyl, —NHCO—C₁-C₃cyanoalkyl,—NHCO—C₃-C₄cycloalkyl, wherein the cycloalkyl is optionally substitutedwith one to two substituents selected from the group consisting offluorine, chlorine, —CN, C₁-C₆alkyl or C₁-C₄alkoxy; —NHCO-phenyl,wherein the phenyl is optionally substituted with one to twosubstituents selected from the group consisting of halogen, —CN,C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy and C₁-C₃haloalkoxy;—NHSO₂—C₁-C₃alkyl, —NHSO₂—C₁-C₃haloalkyl, —CONH(C₁-C₃alkyl),—CON(C₁-C₃alkyl)₂, —CONH—SO₂—C₁-C₃alkyl,—CON(C₁-C₃alkyl)(C₃-C₆cycloalkyl), —CONH(C₁-C₃haloalkyl),—CONH(C₃-C₆cycloalkyl), —CONH(1-cyano-C₃-C₆cycloalkyl), —CONH-phenyl,wherein the phenyl is optionally substituted with one to twosubstituents selected from the group consisting of halogen, —CN,C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy and C₁-C₃haloalkoxy; and (B) thethiazole is optionally substituted with one to two substituents selectedfrom the group consisting of halogen, —CN, —NO₂, C₁-C₆alkyl,C₃-C₆cycloalkyl, C₁-C₃haloalkyl, C₁-C₄alkoxy, C₁-C₃haloalkoxy,C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,C₁-C₃haloalkylthio, C₁-C₃haloalkylsulfinyl and C₁-C₃haloalkylsulfonyl;R₅ is hydrogen, halogen, —CN, C₁-C₃alkyl, C₁-C₃haloalkyl,C₃-C₄cycloalkyl, or C₁-C₃alkoxy.
 4. The compound according to claim 1,wherein X is O or S; Q¹ and Q² are independently CR⁵ or N, provided atleast one of Q¹ and Q² is N; Y is a direct bond or CH₂; R¹ is hydrogen;C₁-C₃alkyl optionally substituted with —CN, —Si(CH₃)₃ or one to threesubstituents selected from the group consisting of fluorine, chlorine orbromine; C₂-C₄alkenyl; C₂-C₄alkynyl; C₃-C₄cycloalkyl-C₁-C₂alkyl- whereinthe C₃-C₄cycloalkyl is optionally substituted with one to twosubstituents selected from the group consisting of fluorine, chlorineand bromine; R² is phenyl or pyridine wherein the phenyl or pyridine issubstituted with one to three substituents, provided at least onesubstituent is on either carbon adjacent to the carbon bonded to the C═Xgroup, each independently selected from the group consisting offluorine, chlorine, bromine, —CN, —NO₂, methyl, cyclopropyl,difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy,difluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, ethylthio,ethylsulfinyl, ethylsulfonyl, isopropylthio, isopropylsulfinyl,isopropylsulfonyl, cyclopropylthio, cyclopropylsulfinyl,cyclopropylsulfonyl, difluoromethylthio, difluoromethylsulfinyl,difluoromethylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl,trifluoromethylsulfonyl, and phenyl, wherein the phenyl is optionallysubstituted with one two substituents selected from the group consistingof fluorine, chlorine, bromine, —CN, difluoromethyl and trifluoromethyl;or R² is phenyl or pyridine, wherein the phenyl or pyridine issubstituted with a total of one to three substituents, provided thesubstituent(s) are not on either carbon adjacent to the carbon bonded tothe C═X group and one substituent is independently selected from group Aconsisting of tert-butyl, cyclopropyl, 1-cyanocyclopropyl, methylthio,methylsulfinyl, methylsulfonyl, ethylthio, ethylsulfinyl, ethylsulfonyl,isopropylthio, isopropylsulfinyl, isopropylsulfonyl, tert-butylthio,tert-butylsulfinyl, tert-butylsulfonyl, cyclopropylthio,cyclopropylsulfinyl, cyclopropylsulfonyl, difluoromethylsulfinyl,difluoromethylsulfonyl, trifluoromethylsulfinyl,trifluoromethylsulfonyl, trifluoroethylsulfinyl, trifluoroethylsulfonyl;phenylsulfonyl wherein the phenyl is optionally substituted with one twosubstituents selected from the group consisting of fluorine, chlorine,bromine, —CN, difluoromethyl and trifluoromethyl; —NHCO-phenyl whereinthe phenyl is optionally substituted with one to two substituentsselected from the group consisting of fluorine, chlorine, CN, methyl andtrifluoromethyl; (cyclopropylamino)carbonyl, 1-(methoxyimino)ethyl,acetamido, (cyclopropylcarbonyl)amino, (phenylsulfonyl)amino; and phenyland 5-membered heteroaryl wherein the phenyl or 5-membered heteroaryl isoptionally substituted with one two substituents selected from the groupconsisting of fluorine, chlorine bromine, —CN, difluoromethyl,trifluoromethyl and trifluoromethoxy; and the other one to two optionalsubstituent(s) are each independently selected from group B consistingof fluorine, chlorine, bromine, —CN, —NO₂, methyl, cyclopropyl,difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy,difluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl,difluoromethylthio, difluoromethylsulfinyl, difluoromethylsulfonyl,trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyland phenyl, wherein the phenyl is optionally substituted with one twosubstituents selected from the group consisting of fluorine, chlorinebromine, —CN, difluoromethyl and trifluoromethyl; or R² is thiophene,furane, pyrazole, thiazole, oxazole or isoxazole each of which isoptionally substituted by one to three substituents independentlyselected from the group consisting of of fluorine, chlorine, bromine,—CN, —NO₂, methyl, cyclopropyl, difluoromethyl, trifluoromethyl,methoxy, trifluoromethoxy, difluoromethoxy, methylthio, methylsulfinyl,methylsulfonyl, difluoromethylthio, difluoromethylsulfinyl,difluoromethylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl,trifluoromethylsulfonyl and phenyl, wherein the phenyl is optionallysubstituted with one two substituents selected from the group consistingof fluorine, chlorine, bromine, —CN, difluoromethyl and trifluoromethylor R² is C₁-C₃alkyl substituted with one substituent selected from thegroup consisting of methoxy, trifluoromethoxy, difluoromethoxy,methylthio, methylsulfinyl, methylsulfonyl, difluoromethylthio,difluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylthio,trifluoromethylsulfinyl, trifluoromethylsulfonyl and phenyl, wherein thephenyl is optionally substituted with one two substituents selected fromthe group consisting of fluorine, chlorine, bromine, —CN, difluoromethyland trifluoromethyl or R² is naphthyl; or pyrazolo[1.5-a]pyridin-2-yl,optionally substituted with trifluoromethyl or chlorine; R^(3a), R^(3b)are independently selected from the group consisting of hydrogen;C₁-C₃alkyl optionally substituted by one to three substituentsindependently selected from the group consisting of methyl, ethyl,iso-propyl, n-propyl, cyclopropyl, cyclobutyl, difluoromethyl,trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy,methylthio, methylsulfinyl, methylsulfonyl, trifluoromethylthio,trifluoromethylsulfinyl, and trifluoromethylsulfonyl; cyclopropyl,difluoromethyl, trifluoromethyl, difluoromethyl, trifluoromethyl,2,2-difluoroethyl, 2,2,2-trifluoroethyl, ethinyl, 2-propen-1-yl and2-propin-1-yl; benzyl wherein the phenyl substituent is optionallysubstituted with one to three substituents independently selected fromthe group consisting of fluorine, chlorine, bromine, —CN, NO₂, methyl,trifluoromethyl and methoxy; heterocyclyl-methyl wherein theheterocyclyl substituent is selected from the group consisting of 4- to10-membered heterocyclyl, 5-membered heteroaryl and 6-memberedheteroaryl, each of which is optionally substituted by one to threesubstituents independently selected from the group consisting offluorine, chlorine, bromine, —CN, —NO₂, methyl, trifluoromethyl andmethoxy; and phenyl optionally substituted with one substituent selectedfrom the group consisting of fluorine, chlorine, bromine, —CN, —NO₂,methyl, trifluoromethyl and methoxy; or R^(3a), R^(3b) form togetherwith the carbon to which they are connected a cyclopropane, cyclobutane,oxetane or tetrahydropyrane ring; R⁴ is pyridine, pyrimidine, pyrazineor thiazole, wherein (A) the pyridine, pyrimidine or pyrazine isoptionally substituted with one to three substituents selected from thegroup consisting of fluorine, chlorine, bromine, —CN, —NH₂, —NO₂, —COOH,—CONH₂, —CSNH₂, —CO₂Me, methyl, ethyl, difluoromethyl, trifluoromethyl,pentafluoroethyl, cyclopropyl, methoxy, difluoromethoxy,trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl,difluoromethylthio, difluoromethylsulfinyl, difluoromethylsulfonyl,trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl,—NHCO-methyl, —NHCO-trifluoromethyl, —NHCO—CH₂CN, —NHCO-cyclopropyl,—NHCO-1-cyanocyclopropyl, —NHSO₂-methyl, —NHSO₂-trifluoromethyl,—NHCO-phenyl, wherein the phenyl is optionally substituted with one totwo substituents selected from the group consisting of fluorine,chlorine, bromine, —CN, methyl, difluoromethyl, trifluoromethyl,methoxy, difluoromethoxy and trifluoromethoxy; —CONH-methyl,—CONH—SO₂-methyl, —CON—(N-methyl)-N-cyclopropyl, —CONH-difluoroethyl,—CONH-trifluoroethyl, —CONH-cyclopropyl, —CONH-1-cyanocyclopropyl,—CONH-phenyl, wherein the phenyl is optionally substituted with one totwo substituents selected from the group consisting of fluorine,chlorine, bromine, —CN, methyl, difluoromethyl, trifluoromethyl,methoxy, difluoromethoxy and trifluoromethoxy; and (B) the thiazole isoptionally substituted with one to two substituents selected from thegroup consisting of fluorine, chlorine, bromine, —CN, —NO₂, methyl,ethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyclopropyl,methoxy, difluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl,methylsulfonyl, difluoromethylthio, difluoromethylsulfinyl,difluoromethylsulfonyl, trifluoromethylthio,trifluoromethylsulfinylandtrifluoromethylsulfonyl; R⁵ is hydrogen,fluorine, chlorine, bromine, —CN, methyl, ethyl, iso-propyl,difluoromethyl, trifluoromethyl, cyclopropyl, methoxy, or ethoxy.
 5. Thecompound according to claim 1, wherein X is O or S; Q¹ is N Q² is CR⁵ Yis a direct bond or CH₂; R¹ is hydrogen, methyl, ethyl,2-(trimethylsilyl)ethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,3,3,3-trifluoropropyl, or cyclopropyl-CH₂—; R²3-chloro-2-fluoro-5-(trifluoromethyl)phenyl,3-chloro-5-(methylsulfonyl)phenyl,3-methylsulfonyl-5-(trifluoromethyl)phenyl,5-(methylsulfonyl)pyridin-3-yl, 3-(methylsulfonyl)phenyl,3-(trifluoromethylsulfonyl)phenyl,5-[(trifluoromethyl)sulfonyl]pyridin-3-yl,3-chloro-5-[(cyclopropylamino)carbonyl]phenyl,3-cyclopropyl-5-(trifluoromethyl)phenyl, 2,3,5-trichlorophenyl,3-phenyl-5-(trifluoromethyl)phenyl,[3-chloro-5-(trifluoromethyl)phenyl]methyl,3-(4-fluorophenyl)-5-(trifluoromethyl)phenyl, 2-chlorophenyl,2,5-dichlorophenyl, 2,3,4-trichlorophenyl, 2,3-dichlorophenyl,2,4-dichlorophenyl, 2,6-difluorophenyl,3-fluoro-5-(trifluoromethylsulfonyl)phenyl,3-chloro-5-(trifluoromethylsulfonyl)phenyl, 5-chloro-3-thienyl,3,4,5-trichloro-2-thienyl, 2,5-dichloro-3-thienyl,4,5-dichloro-2-thienyl, 1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl,4-chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl,5-methyl-1,2-oxazol-3-yl, 5-cyclopropyl-1,2-oxazol-3-yl,3-chloro-1,2-oxazol-5-yl, 2-chloro-1,3-thiazol-5-yl,1-methyl-1H-pyrazol-4-yl, 5-chloro-1-methyl-1H-pyrazol-4-yl,3-chloro-5-cyclopropylsulfonylphenyl,3-chloro-5-(4-fluorophenyl)sulfonylphenyl,3-chloro-5-ethylsulfonylphenyl, 3-cyclopropyl-5-fluorophenyl,3-chloro-5-(isopropylthio)phenyl, 3-chloro-5-(1H-pyrazol-1-yl)phenyl,3-chloro-5-(1H-1,2,4-triazol-1-yl)phenyl, 3-tert-butyl-5-chlorophenyl,3-tert-butyl-5-bromophenyl, 3-fluoro-5-cyclopropylphenyl,3-chloro-5-cyclopropylphenyl, 3-chloro-5-isopropylsulfonylphenyl,1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl,3-cyclopropyl-5-(trifluoromethoxy)phenyl,4-(trifluoromethylsulfonyl)phenyl,3-chloro-5-[1-(methoxyimino)ethyl]phenyl,3-(tert-butylthio)-5-chlorophenyl, 1-(4-fluorophenyl)-1H-pyrazol-4-yl,1-(4-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-3-yl,5-[4-(trifluoromethoxy)phenyl]pyridin-3-yl,3-chloro-5-methylsulfanylphenyl, 3-chloro-5-methylsulfinylphenyl,3-benzamido-5-chlorophenyl, 3-(tert-butylsulfonyl)-5-chlorophenyl,5-[4-(trifluoromethyl)phenyl]-pyridin-3-yl,5-[4-(trifluoromethoxy)phenyl]-pyridin-3-yl,5-(4-chlorophenyl)pyridin-3-yl, 5-(4-fluorophenyl)pyridin-3-yl,3-chloro-5-[(phenylsulfonyl)amino]phenyl, 3-acetamido-5-chlorophenyl,3-chloro-5-[(cyclopropylcarbonyl)amino]phenyl,3-chloro-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl,3-chloro-5-[(2,2,2-trifluoroethyl)sulfonyl]phenyl,3-chloro-5-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl,3,5-bis(methylsulfonyl)phenyl, pyrazolo[1,5-a]pyridin-2-yl,7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl,6-chloropyrazolo[1,5-a]pyridin-2-yl, naphth-2-yl,3-[4′-(trifluoromethoxy)phenyl]-phenyl,3-(4′-fluorophenyl)-5-(trifluoromethyl)phenyl or3-chloro-5-(1-cyanocyclopropyl)phenyl; R^(3a) is hydrogen, methyl ormethoxymethyl; R^(3b) is methyl or methoxymethyl if R^(3a) is hydrogen;R^(3b) is hydrogen if R^(3a) is methyl or methoxymethyl; R^(3a) andR^(3b) form together with the carbon to which they are connected acyclopropane ring; R⁴ is pyridin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl,5-fluoropyrimidin-2-yl, 5-chloropyrimidin-2-yl, 5-cyanopyrimidin-2-yl,5-(trifluoromethyl)pyrimidin-2-yl, 5-methylpyrimidin-2-yl,5-fluoropyridin-2-yl, 5-chloropyridin-2-yl, 2-chloropyridin-4-yl,5-cyanopyridin-2-yl, 4-cyano-pyridin-2-yl, 6-cyano-pyridin-2-yl,5-methoxy-pyridin-2-yl, 5-(trifluoromethyl)-pyridin-2-yl,5-(difluoromethoxy)pyridin-2-yl, 5-(trifluoromethylthio)pyridin-2-yl,5-nitropyridin-2-yl, 5-aminopyridin-2-yl, 3,5-difluoropyridin-2-yl,5-chloro-3-fluoropyridin-2-yl, pyridin-2-yl-5-carboxylic acid, methylpyridin-2-yl-5-carboxylate, N-methyl-pyridin-2-yl-5-carboxamide,N-cyclopropyl-pyridin-2-yl-5-carboxamide,N-cyclopropyl-N-methyl-pyridin-2-yl-5-carboxamide,N-(1-cyanocyclopropyl)-pyridin-2-yl-5-carboxamide,N-(2,2-difluoroethyl)-pyridin-2-yl-5-carboxamide,N-(2,2,2-trifluoroethyl)-pyridin-2-yl-5-carboxamide,N-methylsulfonyl-pyridin-2-yl-5-carboxamide,N-(4-fluorophenyl)-pyridin-2-yl-5-carboxamide, 5-acetamidopyridin-2-yl,5-(trifluoroacetamido)-pyridin-2-yl,5-(2-cyanoacetylamino)-pyridin-2-yl,5-[(cyclopropylcarbonyl)amino]pyridin-2-yl,5-[(1-cyanocyclopropylcarbonyl)amino]-pyridin-2-yl,5-(methanesulfonamido)-pyridin-2-yl,5-(trifluoromethylsulfonamido)-pyridin-2-yl,5-[(4-fluorobenzoyl)amino]pyridine-2-yl pyrazin-2-yl,2-cyano-pyrazin-5-yl, or 1,3-thiazol-2-yl; R⁵ is hydrogen, methyl ortrifluoromethyl.
 6. The compound according to claim 1, comprising astructure according to formula (I′)


7. The compound according to claim 1, wherein Q¹ represents N or CR⁵ andQ² represents N.
 8. The compound according to claim 1, wherein Q¹represents N and Q² represents CR⁵.
 9. A compound of formula (a*)

wherein Y is a direct bond or optionally substituted CH₂; R¹ ishydrogen: C₁-C₆alkyl optionally substituted with one substituentselected from —CN, —CONH₂, —COOH, —NO₂ and —Si(CH₃)₃: C₁-C₆haloalkyl:C₂-C₆alkenyl: C₂-C₆haloalkenyl; C₂-C₆alkynyl; C₂-C₆haloalkynyl;C₃-C₄cycloalkyl-C₁-C₂alkyl- wherein the C₃-C₄cycloalkyl is optionallysubstituted with one or two halogen atoms; oxetan-3-yl-CH₂— or benzyloptionally substituted with halogen or C₁-C₃haloalkyl; R² is phenyl,pyridine, pyrimidine, pyrazine or pyridazine, wherein the phenyl,pyridine, pyrimidine, pyrazine or pyridazine is substituted with one tofive substituents, provided at least one substituent is on either carbonadjacent to the carbon bonded to the C═X group, each independentlyselected from the group consisting of halogen, hydroxy, —NH₂, —CN, —SF₅,—COOH, —CONH₂, —NO₂, and in each case optionally substituted C₁-C₆alkyl,C₃-C₆cycloalkyl, C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₆haloalkyl,C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio, C₃-C₆cycloalkylsulfanyl,C₃-C₆cycloalkylsulfinyl, C₃-C₆cycloalkylsulfonyl,C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, phenylsulfanyl,phenylsulfinyl, phenylsulfonyl, —NH(C₁-C₆alkyl), —N(C₁-C₆alkyl)₂,—NHCO—C₁-C₆alkyl, —N(C₁-C₆alkyl)CO—C₁-C₆alkyl, —NHCO-phenyl,—CO₂C₁-C₆alkyl, —CONH(C₁-C₆alkyl), —CON(C₁-C₆alkyl)₂,—CONH(C₃-C₆cycloalkyl), —CON(C₁-C₆alkyl)(C₃-C₆cycloalkyl),—C(═NOC₁-C₆alkyl)H, —C(═NOC₁-C₆alkyl)-C₁-C₆alkyl; and phenyl and 5- to6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroarylis optionally substituted with one to two substituents, eachindependently selected from the group consisting of halogen, —CN, ineach case optionally substituted C₁-C₆alkyl, C₁-C₆haloalkyl andC₁-C₆alkoxy; and an optionally substituted 4- to 6-membered saturated orpartially unsaturated heterocyclic ring; or R² is phenyl, pyridine,pyrimidine, pyrazine or pyridazine, wherein the phenyl, pyridine,pyrimidine, pyrazine or pyridazine is substituted with a total of one tothree substituents, provided the substituent(s) are not on either carbonadjacent to the carbon bonded to the C═X group and at least one and upto three substituent(s) are independently selected from group Aconsisting of optionally substituted C₄-C₆alkyl; C₁-C₆alkylthio,optionally substituted by one to three substituents independentlyselected from the group consisting of —NH₂, —OH, —NO₂, —CN, —SH,CO₂C₁-C₄alkyl, —CONH₂, SF₅, —SO₂NH₂, C₁-C₄alkyl, C₃-C₄cycloalkyl,C₂-C₄alkenyl, C₅-C₆cycloalkenyl, C₂-C₄alkynyl, —NH(C₁-C₆alkyl),—N(C₁-C₆alkyl)₂, N—C₁-C₄alkanoylamino, C₁-C₄alkoxy, C₁-C₄haloalkoxy,C₂-C₄alkenyloxy, C₂-C₄alkynyloxy, C₃-C₄cycloalkoxy,C₅-C₆cycloalkenyloxy, C₁-C₄alkoxycarbonyl, C₂-C₄alkenyloxycarbonyl,C₂-C₄alkynyloxycarbonyl, C₆—, C₁₀—, C₁₄-aryloxycarbonyl, C₁-C₄alkanoyl,C₂-C₄alkenylcarbonyl, C₂-C₄alkynylcarbonyl, C₆—, C₁₀—, C₁₄-arylcarbonyl,C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₃-C₄cycloalkylthio,C₂-C₄alkenylthio, C₅-C₆cycloalkenylthio, C₂-C₄alkynylthio,C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, C₁-C₄alkylsulfonyl,C₁-C₄haloalkylsulfonyl, —SO₂—NH(C₁-C₆alkyl), —SO₂—N(C₁-C₆alkyl)₂,C₁-C₄alkylphosphinyl, C₁-C₄alkylphosphonyl, N—C₁-C₄alkylaminocarbonyl,N,N-di-C₁-C₄alkylaminocarbonyl, N—C₁-C₄alkanoylaminocarbonyl,N—C₁-C₄alkanoyl-N—C₁-C₄alkylaminocarbonyl, C₆—, C₁₀—, C₁₄-aryl, C₆—,C₁₀—, C₁₄-aryloxy, benzyl, benzyloxy, benzylthio, C₆—, C₁₀—,C₁₄-arylthio, C₆—, C₁₀—, C₁₄-arylamino, benzylamino, heterocyclyl,heteroaryl and trialkylsilyl, substituents bonded via a double bond,such as C₁-C₄alkylidene (e.g. methylidene or ethylidene), an oxo group,an imino group and a substituted imino group; and in each caseoptionally substituted C₄-C₆haloalkylthio, C₄-C₆haloalkoxy, C₄-C₆alkoxy,C₄-C₆haloalkyl, C₃-C₆cycloalkyl, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₃-C₆cycloalkylsulfanyl, C₃-C₆cycloalkylsulfinyl,C₃-C₆cycloalkylsulfonyl, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl,C₂-C₆alkenylsulfanyl, C₂-C₆alkenylsulfinyl, C₂-C₆alkenylsulfonyl,C₂-C₆alkinylsulfanyl, C₂-C₆alkinylsulfinyl, C₂-C₆alkinylsulfonyl,phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, heterocyclylsulfanyl,heterocyclylsulfinyl, heterocyclylsulfonyl, heteroarylsulfanyl,heteroarylsulfinyl, heteroarylsulfonyl, S—C₁-C₆alkylsulfinimidoyl,S—C₃-C₆cycloalkylsulfinimidoyl, S—C₂-C₆alkenylsulfinimidoyl,S—C₂-C₆alkinylsulfinimidoyl, S-phenylsulfinimidoyl,S-heterocyclylsulfinimidoyl, S-heteroarylsulfinimidoyl,S—C₁-C₆alkylsulfonimidoyl, S—C₃-C₆cycloalkylsulfonimidoyl,S—C₂-C₆alkenylsulfonimidoyl, S—C₂-C₆alkinylsulfonimidoyl,S-phenylsulfonimidoyl, S-heterocyclylsulfonimidoyl,S-heteroarylsulfonimidoyl, —NH(C₁-C₆alkyl), —N(C₁-C₆alkyl)₂,—NHCO—C₁-C₆alkyl, —N(C₁-C₆alkyl)CO—C₁-C₆alkyl,—N(C₃-C₆cycloalkyl)CO—C₁-C₆alkyl, —NHCO-phenyl, —N(C₁-C₆alkyl)CO-phenyl,—N(C₃-C₆cycloalkyl)CO-phenyl, —NHCO—C₃-C₆cycloalkyl,—N(C₁-C₆alkyl)CO—(C₃-C₆cycloalkyl),—N(C₃-C₆cycloalkyl)CO—(C₃-C₆cycloalkyl), —NHCO-heteroaryl,—N(C₁-C₆alkyl)CO-heteroaryl, —N(C₃-C₆cycloalkyl)CO-heteroaryl,—NHCO-heterocyclyl, —N(C₁-C₆alkyl)CO-heterocyclyl,—N(C₃-C₆cycloalkyl)CO-heterocyclyl, —CO₂C₁-C₆alkyl, —CONH(C₁-C₆alkyl),—CON(C₁-C₆alkyl)₂, —CONH(C₃-C₆cycloalkyl),—CON(C₁-C₆alkyl)(C₃-C₆cycloalkyl), —CON(C₃-C₆cycloalkyl)₂, —CONH-phenyl,—CON(C₁-C₆alkyl)phenyl, —CON(C₃-C₆cycloalkyl)phenyl, —CONH-heteroaryl,—CON(C₁-C₆alkyl)heteroaryl, —CON(C₃-C₆cycloalkyl)heteroaryl,—CONH-heterocyclyl, —CON(C₁-C₆alkyl)heterocyclyl,—CON(C₃-C₆cycloalkyl)heterocyclyl, —C(═NOC₁-C₆alkyl)H,—C(═NOC₁-C₆alkyl)-C₁-C₆alkyl, —NHSO₂—C₁-C₆alkyl,—N(C₁-C₆alkyl)SO₂—C₁-C₆alkyl, —N(C₃-C₆cycloalkyl)SO₂—C₁-C₆alkyl,—NHSO₂-phenyl, —N(C₁-C₆alkyl)SO₂-phenyl, —N(C₃-C₆cycloalkyl)SO₂-phenyl,—NHSO₂—C₃-C₆cycloalkyl, —N(C₁-C₆alkyl)SO₂—(C₃-C₆cycloalkyl),—N(C₃-C₆cycloalkyl)SO₂—(C₃-C₆cycloalkyl), —NHSO₂-heterocyclyl,—N(C₁-C₄alkyl)SO₂-heterocyclyl, —N(C₃-C₆cycloalkyl)SO₂-heterocyclyl,—NHSO₂-heteroaryl, —N(C₁-C₆alkyl)SO₂-heteroaryl,—N(C₃-C₆cycloalkyl)SO₂-heteroaryl, —SO₂NH(C₁-C₆alkyl),—SO₂N(C₁-C₆alkyl)₂, —SO₂N(C₁-C₆alkyl)(C₃-C₆cycloalkyl),—SO₂NH(C₃-C₆cycloalkyl), —SO₂N(C₃-C₆cycloalkyl)₂, —SO₂NH(phenyl),—SO₂N(C₁-C₆alkyl)(phenyl), —SO₂N(C₁-C₄cycloalkyl)(phenyl),—SO₂NH(heteroaryl), —SO₂N(C₁-C₆alkyl)(heteroaryl),—SO₂N(C₃-C₆cycloalkyl)(heteroaryl), —SO₂NH(heterocyclyl),—SO₂N(C₁-C₄alkyl)(heterocyclyl), —SO₂N(C₃-C₆cycloalkyl)(heterocyclyl);and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl or 5- to6-membered heteroaryl is optionally substituted with one to twosubstituents, each independently selected from the group consisting ofhalogen, —CN, in each case optionally substituted C₁-C₆alkyl,C₁-C₆haloalkyl, C₁-C₆alkoxy and C₁-C₆haloalkoxy; and an optionallysubstituted 4- to 6-membered saturated or partially unsaturatedheterocyclic ring; and —SO₂NH₂; and the other one to two optionalsubstituent(s) are each independently selected from group B consistingof halogen, hydroxy, —NH₂, —CN, —SF₅, —COOH, —CONH₂, —NO₂, and in eachcase optionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl,C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl,phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, —NH(C₁-C₆alkyl),—N(C₁-C₆alkyl)₂, —NHCO—C₁-C₆alkyl, —N(C₁-C₆alkyl)CO—C₁-C₆alkyl,—NHCO-phenyl, —CO₂C₁-C₆alkyl, —CONH(C₁-C₆alkyl), —CON(C₁-C₆alkyl)₂,—CONH(C₃-C₆cycloalkyl), —CON(C₁-C₆alkyl)(C₃-C₆cycloalkyl),—C(═NOC₁-C₆alkyl)H, —C(═NOC₁-C₆alkyl)-C₁-C₆alkyl; and phenyl and 5- to6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroarylis optionally substituted with one to two substituents, eachindependently selected from the group consisting of halogen, —CN, ineach case optionally substituted C₁-C₆alkyl, C₁-C₆haloalkyl andC₁-C₆alkoxy; or R² is naphthyl optionally substituted by one to threesubstituents independently selected from the group consisting ofhalogen, hydroxy, —CN, —COOH, —CONH₂, —NO₂, —SF₅, —NH₂, and in each caseoptionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl,C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₃-C₆cycloalkylsulfanyl, C₃-C₆cycloalkylsulfinyl,C₃-C₆cycloalkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl,C₁-C₆haloalkylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl,—NH(C₁-C₆alkyl), —N(C₁-C₆alkyl)₂, —NHCO—C₁-C₆alkyl,—N(C₁-C₆alkyl)CO—C₁-C₆alkyl, —NHCO-phenyl, —CO₂C₁-C₆alkyl,—CONH(C₁-C₆alkyl), —CON(C₁-C₆alkyl)₂, —C(═NOC₁-C₆alkyl)H,—C(═NOC₁-C₆alkyl)-C₁-C₆alkyl; and phenyl and 5- to 6-memberedheteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl isoptionally substituted with one to two substituents, each independentlyselected from the group consisting of halogen, —CN, in each caseoptionally substituted C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy; or R²is a heterocyclic ring which is selected from the group consisting of 4-to 10-membered saturated and partially unsaturated heterocyclyl,5-membered heteroaryl, 9-membered heteroaryl and 10-membered heteroaryl,each of which is optionally substituted by one to three substituentsindependently selected from the group consisting of halogen, ═O (oxo),hydroxy, —CN, —COOH, —CONH₂, —NO₂, —SF₅, —NH₂, and in each caseoptionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl,C₃-C₆cycloalkyl-C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₃-C₆cycloalkylsulfanyl, C₃-C₆cycloalkylsulfinyl,C₃-C₆cycloalkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl,C₁-C₆haloalkylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl,—NH(C₁-C₆alkyl), —N(C₁-C₆alkyl)₂, —NHCO—C₁-C₆alkyl,—N(C₁-C₆alkyl)CO—C₁-C₆alkyl, —NHCO-phenyl, —CO₂C₁-C₆alkyl,—CONH(C₁-C₆alkyl), —CON(C₁-C₆alkyl)₂, —C(═NOC₁-C₆alkyl)H,—C(═NOC₁-C₆alkyl)-C₁-C₆alkyl; and phenyl and 5- to 6-memberedheteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl isoptionally substituted with one to two substituents, each independentlyselected from the group consisting of halogen, —CN, in each caseoptionally substituted C₁-C₆alkyl, C₁-C₆haloalkyl and C₁-C₆alkoxy; or R²is in each case optionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl orC₁-C₆haloalkyl; R^(3a), R^(3b) are independently selected from the groupconsisting of hydrogen; halogen; —CN; C₁-C₆alkyl optionally substitutedby one to three substituents independently selected from the groupconsisting of halogen, hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, in eachcase optionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy,C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, —NH(C₁-C₆alkyl),—N(C₁-C₆alkyl)₂, —NHCO—C₁-C₆alkyl, —N(C₁-C₆alkyl)CO—C₁-C₆alkyl,—CO₂C₁-C₆alkyl, —CONH(C₁-C₆alkyl), and —CON(C₁-C₆alkyl)₂; optionallysubstituted C₃-C₆cycloalkyl; optionally substituted C₁-C₆haloalkyl;optionally substituted C₂-C₆alkenyl; optionally substitutedC₂-C₆haloalkenyl: optionally substituted C₂-C₆alkynyl; benzyl whereinthe phenyl substituent is optionally substituted with one to fivesubstituents, each independently selected from the group consisting ofhalogen, hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, —SF₅, in each caseoptionally substituted C₁-C₆alkyl, C₁-C₆alkoxy, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, and C₁-C₆alkylsulfonyl; heterocyclyl-C₁-C₆alkylwherein the heterocyclyl substituent is selected from the groupconsisting of 4- to 10-membered saturated and partially unsaturatedheterocyclyl, 5-membered heteroaryl and 6-membered heteroaryl, each ofwhich is optionally substituted by one to three substituentsindependently selected from the group consisting of halogen, ═O (oxo),hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, in each case optionallysubstituted C₁-C₆alkyl, and C₁-C₆alkoxy; phenyl optionally substitutedwith one to five substituents, each independently selected from thegroup consisting of halogen, hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂,—SF₅, in each case optionally substituted C₁-C₆alkyl, C₁-C₆alkoxy,C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, and C₁-C₆alkylsulfonyl; orheterocyclyl wherein the heterocyclyl substituent is selected from thegroup consisting of 4- to 10-membered saturated and partiallyunsaturated heterocyclyl, 5-membered heteroaryl and 6-memberedheteroaryl, each of which is optionally substituted by one to threesubstituents independently selected from the group consisting ofhalogen, ═O (oxo), hydroxy, —CN, —COOH, —CONH₂, —NO₂, —NH₂, in each caseoptionally substituted C₁-C₆alkyl, and C₁-C₆alkoxy; or R^(3a), R^(3b)form together with the carbon to which they are connected aC₃-C₆-carbocyclic or 3- to 6-membered heterocyclic ring system,optionally substituted with one to two substituents, each independentlyselected from the group consisting of halogen, —CN, in each caseoptionally substituted C₁-C₆alkyl, C₁-C₆alkoxy and C₁-C₆haloalkoxy; R⁴is pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl,wherein the pyridine, pyrimidine, pyrazine, pyridazine or 5-memberedheteroaryl is optionally substituted with one to three substituentsselected from the group consisting of halogen, hydroxy, —CN, —COOH,—CO₂—C₁-C₆alkyl, —SO₂NH₂, —CONH₂, —CSNH₂, —NO₂, —NH₂, in each caseoptionally substituted C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl,C₁-C₆haloalkylsulfonyl, C₃-C₆cycloalkylsulfanyl,C₃-C₆cycloalkylsulfinyl, C₃-C₆cycloalkylsulfonyl, C₂-C₄alkenylsulfanyl,C₂-C₄alkenylsulfinyl, C₂-C₄alkenylsulfonyl, C₂-C₄alkinylsulfanyl,C₂-C₄alkinylsulfinyl, C₂-C₄alkinylsulfonyl, phenylsulfanyl,phenylsulfinyl, phenylsulfonyl, S—C₁-C₆alkylsulfinimidoyl,S—C₃-C₆cycloalkylsulfinimidoyl, S—C₂-C₆alkenylsulfinimidoyl,S—C₂-C₆alkinylsulfinimidoyl, S-phenylsulfinimidoyl,S—C₁-C₆alkylsulfonimidoyl, S—C₃-C₆cycloalkylsulfonimidoyl,S—C₂-C₆alkenylsulfonimidoyl, S—C₂-C₆alkinylsulfonimidoyl,S-phenylsulfonimidoyl, —NH(C₁-C₆alkyl), —N(C₁-C₆alkyl)₂,—NHCO—C₁-C₆alkyl, —N(C₁-C₆alkyl)CO—C₁-C₆alkyl,—N(C₃-C₆cycloalkyl)CO—C₁-C₆alkyl, —NHCO—C₃-C₆cycloalkyl,—N(C₁-C₆alkyl)CO—(C₃-C₆cycloalkyl),—N(C₃-C₆cycloalkyl)CO—(C₃-C₆cycloalkyl), —N(C₁-C₆alkyl)CO-phenyl,—N(C₃-C₆cycloalkyl)CO-phenyl, —NHCO-phenyl, —N(CO—C₁-C₆alkyl)₂,—N(CO—C₃-C₆cycloalkyl)₂, —N(CO-phenyl)₂,—N(CO—C₃-C₆cycloalkyl)(CO—C₁-C₆alkyl),—N(CO—C₃-C₆cycloalkyl)(CO-phenyl), —N(CO—C₁-C₆alkyl)(CO-phenyl),—CONH(C₁-C₆alkyl), —CON(C₁-C₆alkyl)₂, —CONH(C₃-C₆cycloalkyl),—CON(C₁-C₆alkyl)(C₃-C₆cycloalkyl), —CON(C₃-C₆cycloalkyl)₂,—CONH—SO₂—C₁-C₆alkyl, —CONH—SO₂-phenyl, —CONH—SO₂—(C₃-C₆cycloalkyl),—CON(C₁-C₆alkyl)-SO₂—C₁-C₆alkyl, —CON(C₁-C₆alkyl)-SO₂-phenyl,—CON(C₁-C₆alkyl)-SO₂—(C₃-C₆cycloalkyl), —CONH-phenyl,—CON(C₁-C₆alkyl)phenyl, —CON(C₃-C₆cycloalkyl)phenyl, —N(SO₂C₁-C₆alkyl)₂,—N(SO₂C₁-C₆haloalkyl)₂, —N(SO₂C₃-C₆cycloalkyl)₂,—N(SO₂C₁-C₆alkyl)SO₂-phenyl, —N(SO₂C₃-C₆cycloalkyl)SO₂-phenyl,—NHSO₂—C₁-C₆alkyl, —NHSO₂—C₁-C₆haloalkyl, —N(C₁-C₆alkyl)SO₂—C₁-C₆alkyl,—N(C₃-C₆cycloalkyl)SO₂—C₁-C₆alkyl, —NHSO₂-phenyl,—N(C₁-C₆alkyl)SO₂-phenyl, —N(C₃-C₆cycloalkyl)SO₂-phenyl,—NHSO₂—C₃-C₆cycloalkyl, —N(C₁-C₆alkyl)SO₂—(C₃-C₆cycloalkyl),—N(C₃-C₆cycloalkyl)SO₂—(C₃-C₆cycloalkyl), —SO₂NH(C₁-C₆alkyl),—SO₂N(C₁-C₆alkyl)₂, —SO₂N(C₁-C₆alkyl)(C₃-C₆cycloalkyl),—SO₂NH(C₃-C₆cycloalkyl), —SO₂N(C₃-C₆cycloalkyl)₂, —SO₂NH(phenyl),—SO₂N(C₁-C₆alkyl)(phenyl), —SO₂N(C₁-C₄cycloalkyl)(phenyl),—C(═NOC₁-C₆alkyl)H and —C(═NOC₁-C₆alkyl)-C₁-C₆alkyl; R⁵ is hydrogen,halogen, —CN, or in each case optionally substituted C₁-C₆alkyl,C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆alkoxyC(O)—, (C₁-C₆alkoxy)₂CH—,—CO₂C₁-C₆alkyl, —CONH(C₁-C₆alkyl), —CON(C₁-C₆alkyl)₂, —NHCO—C₁-C₆alkyl,—N(C₁-C₆alkyl)CO—C₁-C₆alkyl, —C(═NOC₁-C₆alkyl)H, or—C(═NOC₁-C₆alkyl)-C₁-C₆alkyl.
 10. A compound of formula (b*), wherein

E is hydrogen or C₁-C₆alkyl; A is —CN, chlorine or fluorine; L is S, SOor SO₂.
 11. A compound of formula (c*), wherein

E is hydrogen or C₁-C₆alkyl; A is bromine, chlorine, fluorine, —CN ortrifluoromethyl, optionally chlorine.
 12. The compound of formula (d*),wherein

E is hydrogen or C₁-C₆alkyl; A is bromine, chlorine or fluorine,optionally chlorine; L is S, SO or SO₂, optionally S or SO₂, optionallySO₂; J is ethyl, iso-propyl, tert-butyl, cyclopropyl,2,2,2-trifluoroethyl or 4-fluorophenyl; and wherein the compound offormula (d*) is not 3-(ethylsulfanyl)-5-fluorobenzoic acid or3-(tert-butylsulfanyl)-5-fluorobenzoic acid.
 13. A compound which isselected from 3-cyclopropyl-5-(trifluoromethoxy)benzoic acid and methyl3-cyclopropyl-5-(trifluoromethoxy)benzoate.
 14. A formulation,optionally an agrochemical formulation, comprising at least one compoundof formula (I) according to claim
 1. 15. The formulation according toclaim 14, further comprising at least one extender and/or at least onesurface-active substance.
 16. The formulation according to claim 14,wherein the compound of formula (I) is in a mixture with at least onefurther active compound.
 17. A method for controlling one or more pests,optionally animal pests, comprising allowing a compound of formula (I)according to claim 1 or a formulation thereof to act on the pests and/ora habitat thereof.
 18. The method according to claim 17, wherein thepest is an animal pest and comprises an insect, an arachnid or anematode, or the pest is an insect, an arachnid or a nematode.
 19. Aproduct comprising a compound of formula (I) according to claim 1 or ofa formulation thereof for controlling one or more animal pests.
 20. Theproduct according to claim 19, wherein the animal pest comprises aninsect, an arachnid or a nematode, or the animal pest is an insect, anarachnid or a nematode.
 21. The product according to claim 19 in cropprotection.
 22. The product according to claim 19 in the field of animalhealth.
 23. A method for protecting seed or a germinating plant from oneor more pests, optionally animal pests, comprising contacting the seedwith a compound of formula (I) according to claim 1 or with aformulation thereof.
 24. A seed obtained by the method according toclaim 23.